A Concise Diastereoselective Total Synthesis of α-Ambrinol

Mar Drugs. 2023 Apr 1;21(4):230. doi: 10.3390/md21040230.

Abstract

(-)-cis-α-Ambrinol is a natural product present in ambergris, a substance of marine origin that has been highly valued by perfumers. In this paper, we present a new approach to its total synthesis. The starting material is commercially available α-ionone and the key step is an intramolecular Barbier-type cyclization induced by CpTiCl2, an organometallic compound prepared in situ by a CpTiCl3 reduction with Mn.

Keywords: CpTiCl2; ambergris; ambrinol; barbier reaction.

MeSH terms

  • Biological Products*
  • Cyclization
  • Molecular Structure
  • Stereoisomerism

Substances

  • Biological Products