LT4185B - Process for preparing 7-rtialkylsilyl baccatin iii - Google Patents

Process for preparing 7-rtialkylsilyl baccatin iii Download PDF

Info

Publication number: LT4185B
Authority: LT; Lithuania
Prior art keywords: iii; trialkylsilyl; baccatin iii; general formula; formula
Prior art date: 1994-04-05

Application number

LT96-137A

Other languages

English (en)

Lithuanian (lt)

Other versions

LT96137A (en

Inventor

Jean-Pierre Bastart

Jean-Pierre Leconte

Original Assignee

Rhone Poulenc Rorer Sa

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1994-04-05

Filing date

1996-09-24

Publication date

1997-07-25

1996-09-24 Application filed by Rhone Poulenc Rorer Sa filed Critical Rhone Poulenc Rorer Sa

1997-02-25 Publication of LT96137A publication Critical patent/LT96137A/xx

1997-07-25 Publication of LT4185B publication Critical patent/LT4185B/lt

Links

OVMSOCFBDVBLFW-VHLOTGQHSA-N 5beta,20-epoxy-1,7beta,13alpha-trihydroxy-9-oxotax-11-ene-2alpha,4alpha,10beta-triyl 4,10-diacetate 2-benzoate Chemical compound O([C@@H]1[C@@]2(C[C@H](O)C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)O)C(=O)C1=CC=CC=C1 OVMSOCFBDVBLFW-VHLOTGQHSA-N 0.000 title abstract 2
238000004519 manufacturing process Methods 0.000 title abstract 2
YWLXLRUDGLRYDR-ZHPRIASZSA-N 5beta,20-epoxy-1,7beta,10beta,13alpha-tetrahydroxy-9-oxotax-11-ene-2alpha,4alpha-diyl 4-acetate 2-benzoate Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](O)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 YWLXLRUDGLRYDR-ZHPRIASZSA-N 0.000 claims abstract description 24
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 18
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 14
238000000034 method Methods 0.000 claims description 14
-1 alkyl radicals Chemical class 0.000 claims description 10
238000006884 silylation reaction Methods 0.000 claims description 8
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 7
125000004432 carbon atom Chemical group C* 0.000 claims description 6
239000003153 chemical reaction reagent Substances 0.000 claims description 6
150000007530 organic bases Chemical class 0.000 claims description 6
238000006243 chemical reaction Methods 0.000 claims description 3
QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 2
238000002955 isolation Methods 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims 2
239000002904 solvent Substances 0.000 claims 1
229930014667 baccatin III Natural products 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
230000021736 acetylation Effects 0.000 description 3
238000006640 acetylation reaction Methods 0.000 description 3
239000000047 product Substances 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
DCFKHNIGBAHNSS-UHFFFAOYSA-N chloro(triethyl)silane Chemical compound CC[Si](Cl)(CC)CC DCFKHNIGBAHNSS-UHFFFAOYSA-N 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
RQMWVVBHJMUJNZ-UHFFFAOYSA-N 4-chloropyridin-2-amine Chemical group NC1=CC(Cl)=CC=N1 RQMWVVBHJMUJNZ-UHFFFAOYSA-N 0.000 description 1
229930012538 Paclitaxel Natural products 0.000 description 1
229940123237 Taxane Drugs 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000005457 ice water Substances 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
229960001592 paclitaxel Drugs 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000000725 suspension Substances 0.000 description 1
DKPFODGZWDEEBT-QFIAKTPHSA-N taxane Chemical group C([C@]1(C)CCC[C@@H](C)[C@H]1C1)C[C@H]2[C@H](C)CC[C@@H]1C2(C)C DKPFODGZWDEEBT-QFIAKTPHSA-N 0.000 description 1
RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/1892—Preparation; Treatments not provided for in C07F7/20 by reactions not provided for in C07F7/1876 - C07F7/1888
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/188—Preparation; Treatments not provided for in C07F7/20 by reactions involving the formation of Si-O linkages

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Epoxy Compounds (AREA)
Silicon Compounds (AREA)
Crystals, And After-Treatments Of Crystals (AREA)
Peptides Or Proteins (AREA)
Saccharide Compounds (AREA)
Liquid Deposition Of Substances Of Which Semiconductor Devices Are Composed (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Internal Circuitry In Semiconductor Integrated Circuit Devices (AREA)
Processes Of Treating Macromolecular Substances (AREA)
Magnetic Resonance Imaging Apparatus (AREA)
Steroid Compounds (AREA)
Silicon Polymers (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Cephalosporin Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

LT96-137A 1994-04-05 1996-09-24 Process for preparing 7-rtialkylsilyl baccatin iii LT4185B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR9403979A FR2718137B1 (fr)	1994-04-05	1994-04-05	Procédé de préparation de trialcoylsilyl-7 baccatine III.

Publications (2)

Publication Number	Publication Date
LT96137A LT96137A (en)	1997-02-25
LT4185B true LT4185B (en)	1997-07-25

Family

ID=9461745

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LT96-137A LT4185B (en)	1994-04-05	1996-09-24	Process for preparing 7-rtialkylsilyl baccatin iii

Country Status (33)

Country	Link
US (1)	US5670658A (de)
EP (1)	EP0754185B1 (de)
JP (1)	JP3718225B2 (de)
KR (1)	KR100399246B1 (de)
CN (1)	CN1058497C (de)
AT (1)	ATE160351T1 (de)
AU (1)	AU683560B2 (de)
BG (1)	BG62735B1 (de)
BR (1)	BR9507444A (de)
CA (1)	CA2186916C (de)
CZ (1)	CZ288397B6 (de)
DE (1)	DE69501080T2 (de)
DK (1)	DK0754185T3 (de)
EE (1)	EE03240B1 (de)
ES (1)	ES2109103T3 (de)
FI (1)	FI115970B (de)
FR (1)	FR2718137B1 (de)
GE (1)	GEP19991537B (de)
GR (1)	GR3025448T3 (de)
HU (1)	HU214158B (de)
LT (1)	LT4185B (de)
LV (1)	LV11691B (de)
MX (1)	MX9604466A (de)
NO (1)	NO305839B1 (de)
NZ (1)	NZ284490A (de)
PL (1)	PL316588A1 (de)
RO (1)	RO115631B1 (de)
RU (1)	RU2127729C1 (de)
SK (1)	SK280448B6 (de)
TW (1)	TW284765B (de)
UA (1)	UA44730C2 (de)
WO (1)	WO1995026967A1 (de)
ZA (1)	ZA952733B (de)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5973160A (en) *	1992-12-23	1999-10-26	Poss; Michael A.	Methods for the preparation of novel sidechain-bearing taxanes
US7288665B1 (en) *	1997-08-18	2007-10-30	Florida State University	Process for selective derivatization of taxanes
ATE234800T1 (de)	1997-08-21	2003-04-15	Univ Florida State	Verfahren zur synthese von taxanen
AU2001288805A1 (en) *	2000-09-22	2002-04-02	Bristol-Myers Squibb Company	Method for reducing toxicity of combined chemotherapies
ITMI20012185A1 (it) *	2001-10-19	2003-04-19	Indena Spa	Procedimento per la preparazione della 14beta-idrossi-baccatina iii-1,14-carbonato
ITMI20012186A1 (it) *	2001-10-19	2003-04-19	Indena Spa	Procedimento per la preparazione della 14-beta-idrossi-baccatina iii-1,14-carbonato
WO2004033442A2 (en) *	2002-10-09	2004-04-22	Chatham Biotec Ltd.	Novel taxanes and methods related to use and preparation thereof
US7202370B2 (en) *	2003-10-27	2007-04-10	Conor Medsystems, Inc.	Semi-synthesis of taxane intermediates from 9-dihydro-13-acetylbaccatin III
KR20070013300A (ko) *	2004-05-14	2007-01-30	이뮤노젠 아이엔씨	박카틴 ⅲ 화합물의 합성 방법
CZ298333B6 (cs) *	2005-09-26	2007-08-29	Zentiva, A. S	Zpusob prípravy 7-trialkylsilylbaccatinu III
JP5588983B2 (ja)	2008-08-11	2014-09-10	ウェルズファーゴバンクナショナルアソシエイション	マルチアームポリマーアルカノエートコンジュゲート
WO2012088422A1 (en)	2010-12-22	2012-06-28	Nektar Therapeutics	Multi-arm polymeric prodrug conjugates of taxane-based compounds
US10894087B2 (en)	2010-12-22	2021-01-19	Nektar Therapeutics	Multi-arm polymeric prodrug conjugates of cabazitaxel-based compounds
US9199954B2 (en)	2010-12-22	2015-12-01	Nektar Therapeutics	Non-ring hydroxy substituted taxanes and methods for synthesizing the same

Citations (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0336840A1 (de)	1988-04-06	1989-10-11	Centre National De La Recherche Scientifique (Cnrs)	Verfahren zur Herstellung von Taxol
WO1992009589A1 (fr)	1990-11-23	1992-06-11	Rhone-Poulenc Rorer S.A.	Procede de preparation de derives du taxane, nouveaux derives obtenus et compositions pharmaceutiques qui les contiennent

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4823167A (en) *	1986-12-16	1989-04-18	Baxter International Inc.	Catheter calibration device
US5229526A (en) *	1991-09-23	1993-07-20	Florida State University	Metal alkoxides
US5597931A (en) *	1992-03-30	1997-01-28	Sloan-Kettering Institute For Cancer Research	Total synthesis of taxol and analogues thereof
US5475011A (en) *	1993-03-26	1995-12-12	The Research Foundation Of State University Of New York	Anti-tumor compounds, pharmaceutical compositions, methods for preparation thereof and for treatment
US5405972A (en) *	1993-07-20	1995-04-11	Florida State University	Synthetic process for the preparation of taxol and other tricyclic and tetracyclic taxanes
US5449790A (en) *	1994-04-06	1995-09-12	Hauser Chemical Research, Inc.	Preparation of 10-deacetylbaccatin III and 7-protected-10-deacetylbaccatin III derivatives from 10-deacetyl taxol A, 10-deacetyl taxol B, and 10-deacetyl taxol C

1994
- 1994-04-05 FR FR9403979A patent/FR2718137B1/fr not_active Expired - Fee Related
1995
- 1995-03-22 TW TW084102793A patent/TW284765B/zh not_active IP Right Cessation
- 1995-04-03 HU HU9602735A patent/HU214158B/hu unknown
- 1995-04-03 JP JP52546695A patent/JP3718225B2/ja not_active Expired - Lifetime
- 1995-04-03 GE GEAP19953433A patent/GEP19991537B/en unknown
- 1995-04-03 US US08/722,103 patent/US5670658A/en not_active Expired - Lifetime
- 1995-04-03 MX MX9604466A patent/MX9604466A/es unknown
- 1995-04-03 ES ES95916696T patent/ES2109103T3/es not_active Expired - Lifetime
- 1995-04-03 WO PCT/FR1995/000419 patent/WO1995026967A1/fr not_active Ceased
- 1995-04-03 RO RO96-01921A patent/RO115631B1/ro unknown
- 1995-04-03 BR BR9507444A patent/BR9507444A/pt not_active IP Right Cessation
- 1995-04-03 AU AU23096/95A patent/AU683560B2/en not_active Expired
- 1995-04-03 DK DK95916696.8T patent/DK0754185T3/da active
- 1995-04-03 UA UA96093735A patent/UA44730C2/uk unknown
- 1995-04-03 RU RU96120192/04A patent/RU2127729C1/ru active
- 1995-04-03 CN CN95192429A patent/CN1058497C/zh not_active Expired - Lifetime
- 1995-04-03 SK SK1265-96A patent/SK280448B6/sk not_active IP Right Cessation
- 1995-04-03 PL PL95316588A patent/PL316588A1/xx unknown
- 1995-04-03 DE DE69501080T patent/DE69501080T2/de not_active Expired - Lifetime
- 1995-04-03 AT AT95916696T patent/ATE160351T1/de active
- 1995-04-03 EE EE9600143A patent/EE03240B1/xx unknown
- 1995-04-03 CZ CZ19962900A patent/CZ288397B6/cs not_active IP Right Cessation
- 1995-04-03 EP EP95916696A patent/EP0754185B1/de not_active Expired - Lifetime
- 1995-04-03 NZ NZ284490A patent/NZ284490A/en not_active IP Right Cessation
- 1995-04-03 ZA ZA952733A patent/ZA952733B/xx unknown
- 1995-04-03 KR KR1019960705642A patent/KR100399246B1/ko not_active Expired - Fee Related
- 1995-04-03 CA CA002186916A patent/CA2186916C/fr not_active Expired - Lifetime
1996
- 1996-09-24 LT LT96-137A patent/LT4185B/lt not_active IP Right Cessation
- 1996-09-27 NO NO964103A patent/NO305839B1/no not_active IP Right Cessation
- 1996-10-04 BG BG100886A patent/BG62735B1/bg unknown
- 1996-10-04 FI FI964001A patent/FI115970B/fi not_active IP Right Cessation
- 1996-10-07 LV LVP-96-392A patent/LV11691B/lv unknown
1997
- 1997-11-20 GR GR970401504T patent/GR3025448T3/el unknown

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0336840A1 (de)	1988-04-06	1989-10-11	Centre National De La Recherche Scientifique (Cnrs)	Verfahren zur Herstellung von Taxol
WO1992009589A1 (fr)	1990-11-23	1992-06-11	Rhone-Poulenc Rorer S.A.	Procede de preparation de derives du taxane, nouveaux derives obtenus et compositions pharmaceutiques qui les contiennent

Also Published As

Publication number	Publication date
AU2309695A (en)	1995-10-23
HU214158B (hu)	1998-01-28
HU9602735D0 (en)	1996-11-28
GEP19991537B (en)	1999-03-05
FR2718137B1 (fr)	1996-04-26
GR3025448T3 (en)	1998-02-27
WO1995026967A1 (fr)	1995-10-12
MX9604466A (es)	1997-07-31
FI964001A0 (fi)	1996-10-04
EE03240B1 (et)	1999-12-15
EP0754185B1 (de)	1997-11-19
LT96137A (en)	1997-02-25
UA44730C2 (uk)	2002-03-15
CA2186916A1 (fr)	1995-10-12
NO964103L (no)	1996-09-27
AU683560B2 (en)	1997-11-13
DE69501080T2 (de)	1998-04-02
CA2186916C (fr)	2004-05-25
DE69501080D1 (de)	1998-01-02
NO305839B1 (no)	1999-08-02
PL316588A1 (en)	1997-01-20
JPH09512522A (ja)	1997-12-16
CZ288397B6 (en)	2001-06-13
TW284765B (de)	1996-09-01
BG100886A (en)	1998-01-30
FI115970B (fi)	2005-08-31
CN1145073A (zh)	1997-03-12
BR9507444A (pt)	1997-09-16
ZA952733B (en)	1996-01-09
BG62735B1 (bg)	2000-06-30
NZ284490A (en)	1998-08-26
US5670658A (en)	1997-09-23
SK126596A3 (en)	1997-04-09
CZ290096A3 (en)	1997-01-15
LV11691B (en)	1997-06-20
RO115631B1 (ro)	2000-04-28
ATE160351T1 (de)	1997-12-15
ES2109103T3 (es)	1998-01-01
JP3718225B2 (ja)	2005-11-24
LV11691A (lv)	1997-02-20
NO964103D0 (no)	1996-09-27
EP0754185A1 (de)	1997-01-22
CN1058497C (zh)	2000-11-15
RU2127729C1 (ru)	1999-03-20
KR100399246B1 (ko)	2004-02-11
FR2718137A1 (fr)	1995-10-06
SK280448B6 (sk)	2000-02-14
HUT76035A (en)	1997-06-30
FI964001L (fi)	1996-10-04
DK0754185T3 (da)	1998-01-26

Legal Events

Date

Code

Title

Description

2005-01-25

PD9A

Change of patent owner

Owner name: AVENTIS PHARMA S.A., FR

Effective date: 20041206

2015-05-25

MK9A

Expiry of a patent

Effective date: 20150403

Publication	Publication Date	Title
LT4185B (en)	1997-07-25	Process for preparing 7-rtialkylsilyl baccatin iii
RU2088578C1 (ru)	1997-08-27	Способ получения производных баккатина iii или 10-дезацетилбаккатина iii и способ получения производных таксана
JP2002538155A (ja)	2002-11-12	１０−デアセチルバカチンｉｉｉからタキサンを調製する方法
CA2205745C (en)	2006-05-09	Method for the preparation of baccatin iii and derivatives thereof from 10-deacetylbaccatin iii
JP4237490B2 (ja)	2009-03-11	タキサン誘導体の調製方法
JP3423002B2 (ja)	2003-07-07	タキサン誘導体、その調製、及びそれを含有する処方物
JP4068663B2 (ja)	2008-03-26	バッカチン誘導体の選択的保護のための方法及びタキサン合成へのその適用
US6444825B1 (en)	2002-09-03	Process for the preparation of an oxazolidinecarboxylic acid which is useful for preparing therapeutically active taxoids
CN1066144C (zh)	2001-05-23	7－羟基塔三烷的制备方法
US7563914B2 (en)	2009-07-21	Method for preparing paclitaxel
CZ300024B6 (cs)	2009-01-14	Zpusob výroby paclitaxelu
JP4454310B2 (ja)	2010-04-21	１４ベータ−ヒドロキシ−バッカチンｉｉｉ−１，１４−カルボネートの調製方法
JPH01313473A (ja)	1989-12-18	γ―ピロン化合物の製造方法
JP2002121195A (ja)	2002-04-23	１３位置換ミルベマイシン誘導体の製造法
JPH07247291A (ja)	1995-09-26	オカダ酸ラクトン誘導体
JP2001064279A (ja)	2001-03-13	新規なセレン化合物類