Model studies related to CP-225,917: Stereocontrolled generation of the quaternary center

被引：21

作者：

Clive, DLJ ^{[1
]}

Zhang, JH ^{[1
]}

机构：

[1] Univ Alberta, Dept Chem, Edmonton, AB T6G 2G2, Canada

来源：

TETRAHEDRON | 1999年 / 55卷 / 41期

基金：

加拿大自然科学与工程研究理事会;

关键词：

aldols; bridgehead chemistry; lactones; oxy-Cope rearrangements;

D O I：

10.1016/S0040-4020(99)00712-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The enolate derived from ester 15 reacts with diketone 10 stereoselectively (10:1), and the major isomer can be converted into lactone 21. This rearranges in boiling 1,2-dichlorobenzene to afford the tricyclic lactone 22, a model compound which shares with CP-225,917 (1) the bridgehead double bond, the C(5) quaternary center, a C(5) side chain of correct length, and the gamma-lactone subunit. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：12059 / 12068

页数：10

共 31 条

[1]

Armstrong A, 1998, SYNLETT, P552

[2]

BARTLETT PA, 1970, TETRAHEDRON LETT, V46, P4459

[3] An approach to the synthesis of CP-263,114: A remarkably facile silyloxy-cope rearrangement [J].