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Issue 20, 2010
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Heronamides A–C, new polyketide macrolactams from an Australian marine-derived Streptomyces sp. A biosynthetic case for synchronized tandem electrocyclization

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Abstract

A Streptomyces sp. isolated from a shallow water sediment sample collected off Heron Island, Australia, afforded three new polyketide macrolactams, heronamides A–C (1–3). Structures were assigned to the heronamides on the basis of detailed spectroscopic analysis, chemical derivatization and biosynthetic considerations. A plausible biosynthetic pathway is proposed in which key carbocyclic ring transformations proceed via an unprecedented synchronized tandem electrocyclization. This biosynthesis provides a framework for the assignment of complete relative configurations across all heronamides, and inspires an attractive biomimetic strategy for future total syntheses. Heronamide C elicits a dramatic and reversible non-cytotoxic effect on mammalian cell morphology.

Graphical abstract: Heronamides A–C, new polyketide macrolactams from an Australian marine-derived Streptomyces sp. A biosynthetic case for synchronized tandem electrocyclization

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Article information


Submitted
16 Jun 2010
Accepted
22 Jul 2010
First published
23 Aug 2010

Org. Biomol. Chem., 2010,8, 4682-4689
Article type
Paper

Heronamides A–C, new polyketide macrolactams from an Australian marine-derived Streptomyces sp. A biosynthetic case for synchronized tandem electrocyclization

R. Raju, A. M. Piggott, M. M. Conte and R. J. Capon, Org. Biomol. Chem., 2010, 8, 4682
DOI: 10.1039/C0OB00267D

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