Synthesis of 7-oxa-phomopsolide E and its C-4 epimer

被引：67
作者：
Li, MS [1 ]
Scott, J [1 ]
O'Doherty, GA [1 ]
机构：
[1] W Virginia Univ, Dept Chem, Morgantown, WV 26506 USA
来源：
TETRAHEDRON LETTERS | 2004年 / 45卷 / 05期
关键词：
D O I：
10.1016/j.tetlet.2003.11.089
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A flexible, enantioselective route to highly functionalized alpha,beta-unsaturated delta-lactones has been applied to the synthesis of 7-oxa-phomopsolide E and its C-4 epimer. This approach relies on the application of the Noyori asymmetric hydrogenation of furyl ketone to produce the secondary furyl alcohol in high enantioexcess, which can be stereoselectively transformed into alpha,beta-unsaturated-delta-lactones by a short, highly diastereo selective oxidation and reduction sequence. DCC and Mitsunobu coupling were used to introduce the side chains of the two natural product analogs. (C) 2003 Elsevier Ltd. All rights reserved.
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页码：1005 / 1009
页数：5
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