Total Syntheses of (R)-Strongylodiols C and D

J Nat Prod. 2016 Jan 22;79(1):244-7. doi: 10.1021/acs.jnatprod.5b00713. Epub 2016 Jan 6.

Abstract

The first total syntheses of two marine natural products, (R)-strongylodiols C and D, with 99% ee were achieved. The key steps of the strategy include the zipper reaction of an alkyne, the asymmetric alkynylation of an unsaturated aliphatic aldehyde catalyzed with Trost's ProPhenol ligand, and the Cadiot-Chodkiewicz cross-coupling reaction of a chiral propargylic alcohol with a bromoalkyne.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alcohols / chemical synthesis*
  • Alcohols / chemistry
  • Alkynes / chemical synthesis*
  • Alkynes / chemistry
  • Biological Products / chemical synthesis*
  • Biological Products / chemistry
  • Catalysis
  • Ligands
  • Molecular Structure
  • Propanols / chemistry
  • Stereoisomerism

Substances

  • Alcohols
  • Alkynes
  • Biological Products
  • Ligands
  • Propanols
  • strongylodiol C
  • strongylodiol D
  • propargyl alcohol