2. Academic Validation
  3. Total Synthesis of the Antitumor Antibiotic Basidalin

Total Synthesis of the Antitumor Antibiotic Basidalin

  • J Org Chem. 2016 Aug 5;81(15):6883-6. doi: 10.1021/acs.joc.6b01255.
Jaime A M Acosta 1,  Ramesh Muddala 1,  Luiz C A Barbosa 2,  John Boukouvalas 1
Affiliations

Affiliations

  • 1 Department of Chemistry, Pavillon Alexandre-Vachon, Université Laval , 1045 Avenue de la Médecine, Quebec City, Quebec G1V 0A6, Canada.
  • 2 Department of Chemistry, Instituto de Ciências Exatas, Universidade Federal de Minas Gerais (UFMG) , Av. Pres. Antônio Carlos, 6627, Campus Pampulha, Belo Horizonte, 31270-901, MG, Brazil.
PMID: 27347696 DOI: 10.1021/acs.joc.6b01255
Abstract

The first synthesis of the tetronamide Antibiotic basidalin was accomplished in five steps and 39% overall yield from readily available 4-bromo-2-triisopropylsilyloxyfuran and 2-formyl-1,3-dithiane. Highlights include: (i) regio- and stereocontrolled assemblage of a pivotal (Z)-γ-ylidene-β-bromobutenolide intermediate by stereodirected vinylogous aldol condensation (SVAC), (ii) installation of the amino group via aza-Michael addition/elimination, and crucially (iii) facile access to basidalin by late-stage dithiane removal.

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