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

作者：Raju Ritesh; Piggott Andrew M; Conte Melissa M; Capon Robert J^*

来源：Organic and Biomolecular Chemistry, 2010, 8(20): 4682-4689.

DOI：10.1039/c0ob00267d

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.

• 出版日期2010