A chemoenzymatic and fully stereocontrolled total synthesis of the antibacterial natural product (-)-platencin
Date
2015
Authors
Chang, Ee
Schwartz, Brett
Draffan, Alistair
Banwell, Martin
Willis, Anthony
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Wiley-VCH Verlag GMBH
Abstract
The natural product (-)-platencin is a potent antibacterial agent that exerts its effects through a novel mode of action. As such, it is an important lead in the development of next-generation antibacterials that are urgently needed because of the rapidly developing resistance to current therapies. The work reported here concerns the development of a convergent and chemoenzymatic total synthesis of (-)-platencin by methods that should provide access to a range of biologically relevant analogues. The key step involves a thermally promoted and facially selective intramolecular Diels-Alder (IMDA) cycloaddition reaction to give an adduct that embodies the tricarbocyclic core of (-)-platencin. This adduct was elaborated over thirteen steps to the natural product. The substrate for the IMDA reaction was prepared by Stille cross-coupling of a Z-configured alkenylstannane with an iodinated diene obtained in an enantiomerically pure form through the whole-cell biotransformation of iodobenzene.
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Chemistry - An Asian Journal
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Journal article
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2037-12-31
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