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

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

Key words

biosynthesis - natural products - biomimetic synthesis - cyclizations - NMR

References and Notes

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