An approach to the anhydride unit of CP-225,917 and CP-263,114

被引：20

作者：

Clive, DLJ ^{[1
]}

Sun, SY ^{[1
]}

Gagliardini, V ^{[1
]}

Sano, MK ^{[1
]}

机构：

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

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 33期

基金：

加拿大自然科学与工程研究理事会;

关键词：

anhydride; siloxy-Cope rearrangement; Tebbe reagent; bridgehead olefin; quaternary carbon;

D O I：

10.1016/S0040-4039(00)01065-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Compound 1, representing the core structure of CP-225,917, including the anhydride subunit, was prepared by an approach involving siloxy-Cope rearrangement of the strained lactone 18, in which C(15) of the anhydride is already present. The C(14) carbon was introduced at a later stage with the Tebbe reagent. Further elaboration gave homoallylic alcohol 25, which was converted into epoxy aldehyde 27, and then into furan 28. This was transformed efficiently into 1 by the successive action of singlet oxygen, DBU and TPAP. (C) 2000 Elsevier Science Ltd. All rights reserved.

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页码：6259 / 6263

页数：5

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