Total synthesis and stereochemical revision of acortatarins A and B

Org Lett. 2011 Oct 21;13(20):5452-5. doi: 10.1021/ol202121k. Epub 2011 Sep 28.

Abstract

A first total synthesis of acortatarins A, B, and an enantiomer of the proposed structure of acortatarin B is described by using readily available d-sugars. This convergent total synthesis revealed the revision of the absolute configuration of acortatarin A and structural revision of acortatarin B. The key steps involved are regioselective epoxide opening with deprotonated 2,5-disubstituted pyrrole and spiroketalization.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acorus / chemistry
  • Alkaloids / chemical synthesis*
  • Alkaloids / chemistry*
  • Epoxy Compounds
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Morpholines / chemical synthesis*
  • Morpholines / chemistry*
  • Spiro Compounds / chemical synthesis*
  • Spiro Compounds / chemistry*
  • Stereoisomerism

Substances

  • Alkaloids
  • Epoxy Compounds
  • Morpholines
  • Spiro Compounds
  • acortatarin A
  • acortatarin B