Evaluation of asymmetric Diels-Alder approaches for the synthesis of the cyclohexene subunit of CP-225,917 and CP-263,114

被引:8
作者
Armstrong, A [1 ]
Davies, NGM [1 ]
Martin, NG [1 ]
Rutherford, AP [1 ]
机构
[1] Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AZ, England
基金
英国工程与自然科学研究理事会;
关键词
CP-compounds; Diels-Alder; oxazolidinone; cyclopropanation;
D O I
10.1016/S0040-4039(03)00835-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Asymmetric synthesis of a functionalised cyclohexenone required for total synthesis of CP-225,917 and CP-263,114 is reported, using a Lewis acid-promoted Diels-Alder reaction between a 2-sityloxy-1,3-diene and a dienophile bearing an oxazolidinone auxiliary. A novel method for appendage of the exocyclic malonate unit, via cyclopropane ring opening, is also described. (C) 2003 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3915 / 3918
页数:4
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