METHOD FOR EFFECTING THE EQUIVALENT OF A DEMAYO REACTION WITH FORMYL ACETIC ESTER

被引:62
作者
PEARLMAN, BA [1 ]
机构
[1] COLUMBIA UNIV,DEPT CHEM,NEW YORK,NY 10027
关键词
D O I
10.1021/ja00515a039
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Both Woodward reserpine precursor 1 and Corey prostaglandin precursor 3 are monocyclic compounds with vicinal carboxaldehyde and acetic ester appendages. Disconnection of these appendages (along with disconnection of the two oxygen substituents of 1) generates hypothetical precursors (1,4-dihydrobenzoic acid and cis-cyclopentene-3,5-diol) both of which are readily available. Therefore, both reserpine and the prostaglandins might become available by short synthetic sequences if a method existed for the placement of vicinal carboxaldehyde and acetic ester appendages onto double bonds. This paper reports a five-step sequence that accomplishes this transformation for the case of 4-hydroxycyclohexene. © 1979, American Chemical Society. All rights reserved.
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页码:6398 / 6404
页数:7
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