4.6 Article

Total synthesis and stereochemical assignment of bipolamide A acetate

Journal

ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 20, Issue 16, Pages 3348-3358

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d2ob00230b

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Funding

  1. Council of Scientific and Industrial Research, New Delhi
  2. University Grants Commission, New Delhi
  3. SERB, Department of Science and Technology, India [CRG/2019/001664]

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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 stereochemistry of the unassigned C-8 center of the naturally occurring unstable bipolamide A has been unambiguously established through our synthesis.
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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