Methyleniminium salts as acylating agent - One step synthesis of baccatin III from 10-deacetylbaccatin III with high selectivity

被引：9

作者：

Cravallee, C ^{[1
]}

Didier, E ^{[1
]}

Pecquet, P ^{[1
]}

机构：

[1] Rhone Poulenc Rorer SA, Ctr Rech Vitry Alfortville, Dept Procedes Chim, F-94400 Vitry Sur Seine, France

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 24期

关键词：

iminium salts; acylation; regioselection; taxoids;

D O I：

10.1016/S0040-4039(98)00699-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

New methyleniminium salts were investigated as acylating agent of 10-deacetylbaccatin III. Thus, synthesis of baccatin III was performed in one step with 79% isolated yield and 98% selectivity using the iminium salt prepared from mesyl chloride and N-ethylacetamide. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：4263 / 4266

页数：4

共 13 条

[1] BASTARD JP, 1995, Patent No. 9526961
[2] BORNWATER JT, 1912, RECL TRAV CHIM PAY B, V31, P121
[3] CHAUVIERE G, 1981, CR ACAD SCI II, V293, P501
[4] A HIGHLY EFFICIENT, PRACTICAL APPROACH TO NATURAL TAXOL
DENIS, JN
GREENE, AE
GUENARD, D
GUERITTEVOEGELEIN, F
MANGATAL, L
POTIER, P
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (17) : 5917 - 5919
[5] SYNTHESEN MIT AMIDCHLORIDEN .1. REAKTIONEN AN DER FUNKTIONELLEN GRUPPE N.N-DISUBSTITUIERTER CARBONSAUREAMIDCHLORIDE
EILINGSFELD, H
SEEFELDER, M
WEIDINGER, H
[J]. CHEMISCHE BERICHTE-RECUEIL, 1963, 96 (10): : 2671 - &
[6] Guenard D., 1995, CURRENT PHARM DESIGN, V1, P95
[7] CHEMICAL STUDIES OF 10-DEACETYL BACCATIN .3. HEMISYNTHESIS OF TAXOL DERIVATIVES
GUERITTEVOEGELEIN, F
SENILH, V
DAVID, B
GUENARD, D
POTIER, P
[J]. TETRAHEDRON, 1986, 42 (16) : 4451 - 4460
[8] HANSON RL, 1994, Patent No. 629701
[9] Hu SH, 1997, BIOCATAL BIOTRANSFOR, V14, P241
[10] KANTLEHNER W, 1979, IMINIUM SALTS ORGA 2, P65

← 1 2 →