A Pot-Economical Approach to the Total Synthesis of Sch-725674

Org Lett. 2016 Feb 5;18(3):516-9. doi: 10.1021/acs.orglett.5b03547. Epub 2016 Jan 13.

Abstract

A pot-economical total synthesis of antifungal Sch-725674, 1, is reported. The approach takes advantage of a number of one-pot, sequential transformations, including a phosphate tether-mediated one-pot, sequential RCM/CM/chemoselective hydrogenation protocol, a one-pot tosylation/acrylation sequence, and a one-pot, sequential Finkelstein reaction/Boord olefination/acetonide deprotection procedure to streamline the synthesis route by reducing isolation and purification procedures, thus saving time. Overall, an asymmetric route has been developed that is efficiently accomplished in seven pots from phosphate (S,S)-triene and with minimal purification.

Publication types

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

MeSH terms

  • Antifungal Agents / chemical synthesis*
  • Antifungal Agents / chemistry
  • Antifungal Agents / pharmacology
  • Catalysis
  • Hydrogenation
  • Macrolides / chemical synthesis*
  • Macrolides / chemistry
  • Macrolides / pharmacology
  • Molecular Structure
  • Organophosphates
  • Stereoisomerism

Substances

  • Antifungal Agents
  • Macrolides
  • Organophosphates
  • Sch 725674