Synlett 2006(3): 0354-0363  
DOI: 10.1055/s-2006-932453
ACCOUNT
© Georg Thieme Verlag Stuttgart · New York

Elucidation of the Biosynthetic Pathway Leading to the Complex Nonadride Phomoidride B

Gary A. Sulikowski*a, Rongson Pongdeeb
a Department of Chemistry, Vanderbilt University, Nashville, TN 37235-1822, USA
Fax: +1(615)3436199; e-Mail: gary.a.sulikowski@vanderbilt.edu;
b Department of Chemistry, The Colorado College, 14 East Cache La Poudre, Colorado Springs, CO 80903, USA
Further Information

Publication History

Received 29 August 2005
Publication Date:
06 February 2006 (online)

Abstract

In this Account we recall our studies into the biosynthesis of the complex fungal secondary metabolite phomoidride B (also known as CP-263,114). Our labeling studies revealed this natural product is produced by a remarkable dimerization of a sixteen-carbon anhydride. This unique biosynthetic pathway provides new ­opportunities in the area of combinatorial biosynthesis for the production of structurally novel unnatural products.

1 Introduction

1.1 Discovery and Classification of the Phomoidrides

1.2 Proposed Biosynthesis

2 Production of Phomoidrides A-D

2.1 A False Start

2.2 Classification of Phomoidride Producer

2.3 Regulation of Phomoidride Production

3 Labeling Studies with Small Molecule Precursors

4 Proving the C16+C16 Dimerization

5 Future Directions

    References and Notes

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