Enantioselective formal synthesis of tridemethylisovelleral

被引：6
|
作者：
Rome, Daniel [1 ]
Johansson, Martin [1 ]
Sterner, Olov [1 ]
机构：
[1] Lund Univ, Div Organ Chem, S-22100 Lund, Sweden
来源：
TETRAHEDRON LETTERS | 2007年 / 48卷 / 04期
关键词：
D O I：
10.1016/j.tetlet.2006.11.122
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A simple and efficient synthetic route to the bicyclic alpha,beta-unsaturated beta-keto ester methyl (3aS,7aS)-6-oxo-2,3,3a,6,7,7ahexahydro-1H-indene-5-carboxylate, a versatile intermediate in the synthesis of biologically active unsaturated 1,4-dialdehydes, is described. The synthesis includes a chirality introducing nonenzymatic asymmetric desymmetrization (ADS) reaction of a cyclic nieso-anhydride 4 and a modified Hofmann method for preparing exocyclic dienes. The ester was synthesized in a moderate overall yield (19%) from 6 and with an excellent enantioselectivity (> 90%). (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码：635 / 638
页数：4
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