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. 2004 Feb 21;2(4):466-73.
doi: 10.1039/b314816e. Epub 2004 Jan 28.

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

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

William P D Goldring et al. Org Biomol Chem. .

Abstract

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

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