A SIMPLE SYNTHESIS OF 10-DEACETOXYTAXOL DERIVATIVES

被引：39

作者：

HOLTON, RA

SOMOZA, C

CHAI, KB

机构：

[1] Dittmer Laboratory, Chemistry Florida State University Tallahassee

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 11期

关键词：

D O I：

10.1016/0040-4039(94)88314-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The C-10 oxygen substituent can be reductively removed in high yield by reaction of taxol, baccatin III, or 10-deacetylbaccatin III with samanium diiodied. This reaction pathway can be completely shut down by protection of the C-7 hydroxyl group of baccatin III as the triethylsilyl ether.

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页码：1665 / 1668

页数：4

相关论文

共 28 条

[1]

BLECHERT S, 1990, ALKALOIDS CHEM PHARM, V39, P195

[2] SYNTHESIS OF 10-DEACETOXYTAXOL AND 10-DEOXYTAXOTERE [J].

CHAUDHARY, AG ;

KINGSTON, DGI .

TETRAHEDRON LETTERS, 1993, 34 (31) :4921-4924

[3] A FACILE SYNTHESIS OF 7,10-DIDEOXY TAXOL AND 7-EPI-10-DEOXY TAXOL [J].

CHEN, SH ;

WEI, JM ;

VYAS, DM ;

DOYLE, TW ;

FARINA, V .

TETRAHEDRON LETTERS, 1993, 34 (43) :6845-6848

[4] SERENDIPITOUS SYNTHESIS OF A CYCLOPROPANE-CONTAINING TAXOL ANALOG VIA ANCHIMERIC PARTICIPATION OF AN UNACTIVATED ANGULAR METHYL-GROUP [J].

CHEN, SH ;

HUANG, S ;

WEI, JM ;

FARINA, V .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (17) :4520-4521

[5] THE CHEMISTRY OF TAXANES - REACTION OF TAXOL AND BACCATIN DERIVATIVES WITH LEWIS-ACIDS IN APROTIC AND PROTIC MEDIA [J].

CHEN, SH ;

HUANG, S ;

WEI, JM ;

FARINA, V .

TETRAHEDRON, 1993, 49 (14) :2805-2828

[6] TAXOL STRUCTURE-ACTIVITY-RELATIONSHIPS - SYNTHESIS AND BIOLOGICAL EVALUATION OF 10-DEOXYTAXOL [J].

CHEN, SH ;

FAIRCHILD, C ;

MAMBER, SW ;

FARINA, V .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (11) :2927-2928

[7] IMPROVED PROTECTION AND ESTERIFICATION OF A PRECURSOR OF THE TAXOTERE(R) AND TAXOL SIDE-CHAINS [J].

COMMERCON, A ;

BEZARD, D ;

BERNARD, F ;

BOURZAT, JD .

TETRAHEDRON LETTERS, 1992, 33 (36) :5185-5188

[8] THE CHEMISTRY OF TAXANES - UNEXPECTED REARRANGEMENT OF BACCATIN-III DURING CHEMOSELECTIVE DEBENZOYLATION WITH BU3SNOME/LICL [J].

FARINA, V ;

HUANG, S .

TETRAHEDRON LETTERS, 1992, 33 (28) :3979-3982

[9] PHASE-II TRIAL OF TAXOL, AN ACTIVE-DRUG IN THE TREATMENT OF METASTATIC BREAST-CANCER [J].

HOLMES, FA ;

WALTERS, RS ;

THERIAULT, RL ;

FORMAN, AD ;

NEWTON, LK ;

RABER, MN ;

BUZDAR, AU ;

FRYE, DK ;

HORTOBAGYI, GN .

JOURNAL OF THE NATIONAL CANCER INSTITUTE, 1991, 83 (24) :1797-1805

[10]

HOLTON R, 1991, Patent No. 5015744