Total Synthesis of Chiral Falcarindiol Analogues Using BINOL-Promoted Alkyne Addition to Aldehydes

Molecules. 2016 Jan 19;21(1):E112. doi: 10.3390/molecules21010112.

Abstract

An enantioselective total synthesis of chiral falcarindiol analogues from buta-1,3-diyn-1-yltriisopropylsilane is reported. The key step in this synthesis is BINOL-promoted asymmetric diacetylene addition to aldehydes. The two chiral centers of the falcarindiol analogues can be produced by using the same kind of catalyst with high selectivity, and the final product can be obtained in only six steps.

Keywords: BINOL; alkyne; asymmetric addition; diynol; falcarindiol analogues; total synthesis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry*
  • Alkynes / chemistry*
  • Catalysis
  • Diynes / chemical synthesis
  • Diynes / chemistry*
  • Esters
  • Fatty Alcohols / chemical synthesis
  • Fatty Alcohols / chemistry*
  • Molecular Structure
  • Naphthols / chemistry*

Substances

  • Aldehydes
  • Alkynes
  • BINOL, naphthol
  • Diynes
  • Esters
  • Fatty Alcohols
  • Naphthols
  • falcarindiol