MACROLACTONIZATION-TRANSANNULAR ALDOL CONDENSATION APPROACH TO THE TAXANE AB RING-SYSTEM

被引：24

作者：

CHAI, KB ^{[1
]}

SAMPSON, P ^{[1
]}

机构：

[1] KENT STATE UNIV,DEPT CHEM,KENT,OH 44242

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 24期

关键词：

D O I：

10.1021/jo00076a049

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cyclohexenone 13, containing the fully elaborated taxane A ring, was prepared from 4,4-dimethyl-2-cyclohexenone (43% for four steps); two copper-catalyzed Grignard conjugate addition reactions on crowded dienones 8 and 11 were employed as key transformations. Elaboration of 13 to the chloro keto acid 6 was achieved via an epoxidation/regioselective chloride-mediated epoxide ring opening/Jones oxidation protocol (42% for three steps). Macrolactonization (59%) followed by chemoselective transannular aldol condensation within the resulting 11-membered bicyclic keto lactone 4 under thermodynamic control (51%) resulted in closure of the taxane B ring to afford the target 2(5H)-furanone 3.

引用

页码：6807 / 6813

页数：7

共 77 条

[61] A READY SYNTHESIS OF INTERMEDIATES CONTAINING THE A-RING SUBSTRUCTURE OF TAXOL - A DIELSALDER ROUTE TO THE B-SECO TAXANE SERIES (JOURNAL OF ORGANIC-CHEMISTRY, VOL 57, PG 4044, 1992) [J].