Total Synthesis of the Antitumor Antibiotic Basidalin

J Org Chem. 2016 Aug 5;81(15):6883-6. doi: 10.1021/acs.joc.6b01255. Epub 2016 Jul 7.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry
  • Antibiotics, Antineoplastic / chemical synthesis*
  • Antibiotics, Antineoplastic / chemistry*
  • Furans / chemical synthesis
  • Furans / chemistry
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Polyketides / chemistry*
  • Quinolizines / chemistry
  • Stereoisomerism
  • Sulfur Compounds / chemistry

Substances

  • Aldehydes
  • Antibiotics, Antineoplastic
  • Furans
  • Polyketides
  • Quinolizines
  • Sulfur Compounds
  • dithiane
  • hippolachnin A
  • basidalin
  • 3-hydroxybutanal