A facile two-step chemoenzymatic access to natural germination inhibitor (+)-erigeronic acid A

被引：10
作者：
Gogoi, S [1 ]
Argade, NP [1 ]
机构：
[1] Natl Chem Lab, Div Organ Chem Synth, Pune 411008, Maharashtra, India
来源：
TETRAHEDRON | 2006年 / 62卷 / 13期
关键词：
natural germination inhibitor; (+)-erigeronic acid; (R)acetoxysuccinic anhydride; primary enolate of butyl methyl ketone; synthesis;
D O I：
10.1016/j.tet.2006.01.044
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A facile two-step synthesis of natural germination inhibitor 5-butyl-3-oxo-2,3-dihydrofuran-2-yl-acetic acid [(+)-erigeronic acid A, 1] has been described via highly regioselective ring opening of (R)-acetoxysuccinic anhydride with the primary enolate of butyl methyl ketone, followed by an enzymatic hydrolysis and ail in situ dehydrative cyclization pathway with 77% overall yield. Oil the basis of the present chemoenzymatic approach, (R)-configuration has been assigned to the C-2 chiral centre of the natural erigeronic acid. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码：2999 / 3003
页数：5
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