Formal synthesis of Abyssomicin C

被引:41
作者
Couladouros, Elias A.
Bouzas, Emmanuel A.
Magos, Alexandros D.
机构
[1] Agr Univ Athens, Chem Labs, Athens 11855, Greece
[2] NCSR Demokritos, Lab Nat Prod Synth & Bioorgan Chem, Athens 15310, Greece
关键词
D O I
10.1016/j.tet.2006.01.106
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An alternative strategy towards Abyssomicin C(1) is described. The key ene-diene intermediate is synthesized via a Kishi type coupling of an E/Z mixture of triene-iodide 7 and a suitably functionalized derivative of 2,4-dimethylglutaric acid. A final in situ isomerization/intramolecular Diels-Alder cyclization resulted in the formation of the known intermediate 3 as a single isomer in high yield. Further heating of 3 using excess of iodine, afforded iodo-derivative 23, having the entire carbon skeleton of Abyssomicin D. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5272 / 5279
页数:8
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