Issue 22, 2003
From the journal:

Organic & Biomolecular Chemistry

A total synthesis of (±)-phomactin A

Christopher M. Diaper,a   William P. D. Goldringa  and  Gerald Pattenden*a  

* Corresponding authors

a School of Chemistry, The University of Nottingham, University Park, Nottingham, UK
E-mail: gp@nottingham.ac.uk
Fax: +44 (0)115 951 3535
Tel: +44 (0)115 951 3530

Abstract

A total synthesis of the PAF antagonist phomactin A (1), isolated from the marine fungus Phoma sp. is described. The synthesis is based on a Cr(II)/Ni(II) macrocyclisation from the aldehyde vinyl iodide 14, leading to the key phomactatrienol intermediate 16a, followed by elaboration of 16a to the epoxyketone 21, which undergoes spontaneous pyran and hemiacetal ring formation to 1 on deprotection with DDQ.

Graphical abstract: A total synthesis of (±)-phomactin A

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Article information

DOI
https://doi.org/10.1039/B307986D
Article type
Paper
Submitted
16 Jul 2003
Accepted
29 Aug 2003
First published
07 Oct 2003

Org. Biomol. Chem., 2003,1, 3949-3956

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A total synthesis of (±)-phomactin A

C. M. Diaper, W. P. D. Goldring and G. Pattenden, Org. Biomol. Chem., 2003, 1, 3949 DOI: 10.1039/B307986D

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