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

来源：

TETRAHEDRON | 2006年 / 62卷 / 22期

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.

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页码：5272 / 5279

页数：8

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