Synthesis of (±)-tetrapetalone A-Me aglycon

Angew Chem Int Ed Engl. 2014 Aug 25;53(35):9334-8. doi: 10.1002/anie.201404410. Epub 2014 Jul 7.

Abstract

The first synthesis of (±)-tetrapetalone A-Me aglycon is described. Key bond-forming reactions include Nazarov cyclization, a ring-closing metathesis promoted with complete diastereoselectivity by a chiral molybdenum-based complex, tandem conjugate reduction/intramolecular aldol cyclization, and oxidative dearomatization.

Keywords: cross-coupling; cyclization; metathesis; natural products; polycycles.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cyclization
  • Glycosides / chemical synthesis*
  • Glycosides / chemistry
  • Heterocyclic Compounds, 4 or More Rings / chemical synthesis*
  • Heterocyclic Compounds, 4 or More Rings / chemistry
  • Molecular Conformation
  • Molybdenum / chemistry
  • Organometallic Compounds / chemistry
  • Stereoisomerism

Substances

  • Glycosides
  • Heterocyclic Compounds, 4 or More Rings
  • Organometallic Compounds
  • tetrapetalone A
  • Molybdenum