New preparation of (3aR*,6S*,7aR*)-6,7,7-trimethylhexahydro-2-benzofuran-1(3H)-one:: formal synthesis of (±)-γ-irone

被引：5
|
作者：
Gosselin, P [1 ]
Perrotin, A [1 ]
Mille, S [1 ]
机构：
[1] Univ Maine, UMR 6011 CNRS, Organ Synth Lab, F-72085 Le Mans 9, France
来源：
TETRAHEDRON | 2001年 / 57卷 / 04期
关键词：
bicyclic compounds; stereoselective synthesis; hemiester; lactone; (+/-)-gamma-irones;
D O I：
10.1016/S0040-4020(00)01059-0
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A four-step synthesis of (3aR*,6S*,7aR*)-6,7.7-trimethylhexahydro-2-benzofuran-1(3H)-one 2 has been developed. Lactone 2 is an intermediate in a synthesis of gamma -irone. Opening of the Diels-Alder adduct 5 with ethanol afforded hemiester 6b with 87:13 regioselectivity. Subsequent chemoselective reduction of the ester group in 6b yielded hydroxyacid 14 which was lactonized to the cis-fused bicyclic lactone 15. Finally, hydrogenation of 15 into 2 occured with complete diastereoselectivity. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：733 / 738
页数：6
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