SYNTHESES OF ISOCARBACYCLIN BY HIGHLY REGIOSELECTIVE ALKYLATION OF ALLYLIC ALCOHOLS

被引:32
作者
BANNAI, K
TANAKA, T
OKAMURA, N
HAZATO, A
SUGIURA, S
MANABE, K
TOMIMORI, K
KATO, Y
KUROZUMI, S
NOYORI, R
机构
[1] TEIJIN LTD,BIOMED RES LABS 1,HINO,TOKYO 191,JAPAN
[2] NAGOYA UNIV,DEPT CHEM,CHIKUSA KU,NAGOYA,AICHI 464,JAPAN
关键词
D O I
10.1016/S0040-4020(01)87859-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Syntheses of isocarbacyclin (20) using highly regioselective alkylation of the new allylic alcohol intermediate 6 having an exocyclic double bond are described. The allylic alcohol 6 was prepared by (i) allylic rearrangement of the allylic alcohol 3 having an endocyclic double bond and (ii) reductive cyclization of γ-ethynyl aldehyde 11a which was synthesized from (R)-4-hydroxy-2- cyclopentenone derivative 1 in 5 steps. γ-Alkylation of the allylic alcohol 6 was achieved by the use of Murahashi's method to result in the highly regioselective formation of isocarbacyclin (regioselectivity 99%). α-Alkylation of the allylic alcohol 3 was also achieved to construct isocarbacyclin. © 1990.
引用
收藏
页码:6689 / 6704
页数:16
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