Issue 4, 2004

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

Abstract

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 β-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 α-alcohol ‘phomactin’ structure 4, known as Sch 49028, followed by spontaneous pyran ring formation.

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

Article information

Article type
Paper
Submitted
18 Nov 2003
Accepted
15 Dec 2003
First published
28 Jan 2004

Org. Biomol. Chem., 2004,2, 466-473

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

W. P. D. Goldring and G. Pattenden, Org. Biomol. Chem., 2004, 2, 466 DOI: 10.1039/B314816E

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements