Results
Title

A Concise Diastereoselective Total Synthesis of α-Ambrinol.

Authors

López-Martínez, Josefa L.; Torres-García, Irene; Moreno-Gutiérrez, Irene; Oña-Burgos, Pascual; Rosales Martínez, Antonio; Muñoz-Dorado, Manuel; Álvarez-Corral, Míriam; Rodríguez-García, Ignacio

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.

Subjects

ORGANOMETALLIC compounds; NATURAL products; BARBIER reactions; PERFUMERS; RING formation (Chemistry)

Publication

Marine Drugs, 2023, Vol 21, Issue 4, p230

ISSN

1660-3397

Publication type

Academic Journal

DOI

10.3390/md21040230