2. Academic Validation
  3. Synthesis of angiolam A

Synthesis of angiolam A

  • Org Lett. 2014 Jan 17;16(2):548-51. doi: 10.1021/ol403423r.
Marc Timo Gieseler 1,  Markus Kalesse
Affiliations

Affiliation

  • 1 Institute for Organic Chemistry and Centre of Biomolecular Drug Research (BMWZ), Leibniz Universität Hannover , Schneiderberg 1B, 30167 Hannover, Germany.
PMID: 24341445 DOI: 10.1021/ol403423r
Abstract

The first total synthesis of angiolam A has been accomplished in 18 steps. Key steps include vinylogous Mukaiyama aldol reactions of aldehyde-derived dienol ethers, conjugate reduction of the resulting double bond followed by diastereoselective protonation and the Witzeman protocol for macrolactamization. Comparison of the optical rotation of the synthesized material with the isolation data established that the absolute configuration of angiolam A is opposite from the proposed structure.

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