TOTAL SYNTHESIS OF MAYTANSINOIDS - APPROACH TO 4,6-BISDEMETHYLMAYTANSINE AND 4-DEMETHYLMAYTANSINE

被引：6

作者：

BENECHIE, M ^{[1
]}

DELPECH, B ^{[1
]}

QUI, KH ^{[1
]}

KHUONGHUU, F ^{[1
]}

机构：

[1] CNRS,INST CHIM SUBST NAT,F-91198 GIF SUR YVETTE,FRANCE

来源：

TETRAHEDRON | 1992年 / 48卷 / 10期

关键词：

D O I：

10.1016/S0040-4020(01)88513-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A convergent strategy was elaborated to synthesize maytansine 1 and maytansinoids modified on the carbon skeleton, especially 4-demethylmaytansine 2, 6-demethylmaytansine 3, 4,6-bisdemethylmaytansine 4. In this paper, the feasibility of the project was verified by the preparation of key intermediates for the synthesis of 4, 6-bisdemethylmaytansine and 6-demethylmaytansine. The C-1-N open chain compound 18 in the 4,6-bisdemethyl series was obtained.

引用

页码：1895 / 1910

页数：16

共 52 条

[1] STUDIES RELATED TO THE SYNTHESIS OF MAYTANSINOIDS [J].

BARTON, DHR ;

BENECHIE, M ;

KHUONGHUU, F ;

POTIER, P ;

REYNAPINEDO, V .

TETRAHEDRON LETTERS, 1982, 23 (06) :651-654

[2] RESEARCHES ON ACETYLENIC COMPOUNDS .42. REDUCTIONS WITH LITHIUM ALUMINIUM HYDRIDE [J].

BATES, EB ;

JONES, ERH ;

WHITING, MC .

JOURNAL OF THE CHEMICAL SOCIETY, 1954, (JUN) :1854-1860

[3]

BAYER O, 1954, METHODEN ORGANISCHEN, V7, P371

[4] BETA-DIPHENYLPHOSPHINOYL KETONES (PH2PO.CH2CH2CO.R) - STABLE REAGENTS FOR BETA-KETOCARBANIONS [J].

BELL, A ;

DAVIDSON, AH ;

EARNSHAW, C ;

NORRISH, HK ;

TORR, RS ;

WARREN, S .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1978, (22) :988-989

[5] SYNTHESIS OF BETA-(DIPHENYLPHOSPHINOYL) KETONES [J].

BELL, A ;

DAVIDSON, AH ;

EARNSHAW, C ;

NORRISH, HK ;

TORR, RS ;

TROWBRIDGE, DB ;

WARREN, S .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (12) :2879-2891

[6]

BRETT D, 1969, CHEM IND-LONDON, P1017

[7]

CHAHINIAN AP, 1983, CANCER TREAT REP, V67, P401

[8] TOTAL SYNTHESIS OF MAYTANSINE [J].

COREY, EJ ;

WEIGEL, LO ;

CHAMBERLIN, AR ;

CHO, H ;

HUA, DH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (21) :6613-6615

[9]

COREY EJ, 1978, TETRAHEDRON LETT, P1051

[10] READILY ACCESSIBLE 12-I-5 OXIDANT FOR THE CONVERSION OF PRIMARY AND SECONDARY ALCOHOLS TO ALDEHYDES AND KETONES [J].

DESS, DB ;

MARTIN, JC .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (22) :4155-4156

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