En route to a plant scale synthesis of the promising antitumor agent 12,13-desoxyepothilene B

被引：44

作者：

Chappell, MD

Stachel, SJ

Lee, CB

Danishefsky, SJ

机构：

[1] Sloan Kettering Inst Canc Res, Bioorgan Chem Lab, New York, NY 10021 USA

[2] Columbia Univ, Dept Chem, New York, NY 10027 USA

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 11期

关键词：

D O I：

10.1021/ol0059302

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Efficient and processable syntheses of key building blocks of the antitumor agent 12,13-desoxyepothilone B (dEpoB) by catalytic asymmetric induction are herein described.

引用

页码：1633 / 1636

页数：4

共 51 条

[1]

BABLER JN, 1976, TETRAHEDRON LETT, V4, P239

[2] STEREOCONTROLLED TOTAL SYNTHESIS OF "1-ALPHA,25-DIHYDROXYCHOLECALCIFEROL AND 1-ALPHA,25-DIHYDROXYERGOCALCIFEROL [J].

BAGGIOLINI, EG ;

IACOBELLI, JA ;

HENNESSY, BM ;

BATCHO, AD ;

SERENO, JF ;

USKOKOVIC, MR .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (16) :3098-3108

[3] Total synthesis of (-)-epothilone A [J].

Balog, A ;

Meng, DF ;

Kamenecka, T ;

Bertinato, P ;

Su, DS ;

Sorensen, EJ ;

Danishefsky, S .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (23-24) :2801-2803

[4]

Balog A, 1998, ANGEW CHEM INT EDIT, V37, P2675, DOI 10.1002/(SICI)1521-3773(19981016)37:19<2675::AID-ANIE2675>3.0.CO

[5]

2-O

[6] SYNTHESIS OF (S)-(+)-MEVALONOLACTONE AND MEVALONATE ANALOGS [J].

BOLITT, V ;

MIOSKOWSKI, C ;

BHATT, RK ;

FALCK, JR .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (13) :4238-4240

[7]

BOLLAG DM, 1995, CANCER RES, V55, P2325

[8] Desoxyepothilone B is curative against human tumor xenografts that are refractory to paclitaxel [J].

Chou, TC ;

Zhang, XG ;

Harris, CR ;

Kuduk, SD ;

Balog, A ;

Savin, KA ;

Bertino, JR ;

Danishefsky, SJ .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1998, 95 (26) :15798-15802

[9] Desoxyepothilone B:: An efficacious microtubule-targeted antitumor agent with a promising in vivo profile relative to epothilone B [J].

Chou, TC ;

Zhang, XG ;

Balog, A ;

Su, DS ;

Meng, DF ;

Savin, K ;

Bertino, JR ;

Danishefsky, SJ .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1998, 95 (16) :9642-9647

[10] ASYMMETRIC OXYGENATION OF CHIRAL IMIDE ENOLATES - A GENERAL-APPROACH TO THE SYNTHESIS OF ENANTIOMERICALLY PURE ALPHA-HYDROXY CARBOXYLIC-ACID SYNTHONS [J].

EVANS, DA ;

MORRISSEY, MM ;

DOROW, RL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (14) :4346-4348

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