Total synthesis and stereochemical assignment of bipolamide A acetate.

Asymmetric total synthesis of an acetate analogue of the endophytic unstable secondary metabolite bipolamide A has been achieved for the first time adopting a convergent approach. The key feature of this synthesis includes Evans's asymmetric ethylation, Wittig olefination, Takai olefination, stereoselective Grignard addition and intermolecular Heck coupling. This eventually developed a synthetic route of the rarely found branched amine bearing an acyloin moiety. Our synthesis finally established unambiguously the stereochemistry of the unassigned C-8 center of the naturally occurring unstable bipolamide A.

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Sourya Shankar Auddy, Sanu Saha, Rajib Kumar Goswami. Total synthesis and stereochemical assignment of bipolamide A acetate. Organic & biomolecular chemistry. 2022 Apr 20;20(16):3348-3358

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PMID: 35352738

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