Total synthesis of (±)-phomactin G, a platelet activating factor antagonist from the marine fungus Phoma sp.

被引：29

作者：

Goldring, WPD ^{[1
]}

Pattenden, G ^{[1
]}

机构：

[1] Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2004年 / 2卷 / 04期

关键词：

D O I：

10.1039/b314816e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A total synthesis of phomactin G (3), which is a central intermediate in the biosynthesis of phomactin A (5) in Phoma sp. is described. The synthesis is based on a Cr(II)/Ni(II) macrocyclisation from the aldehyde vinyl iodide 9, leading to 16, followed by sequential conversion of 16 into the beta-epoxide 21 and the ketone 25 which, on deprotection, led to (+/-)-phomactin G. Phomactin G (3) shares an interesting structural homology with phomactin D (2), the most potent PAF-antagonist metabolite in Phoma sp. It is most likely converted into phomactin A (5), by initial allylic oxidation to the transient alpha-alcohol 'phomactin' structure 4, known as Sch 49028, followed by spontaneous pyran ring formation.

引用

页码：466 / 473

页数：8

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