A Concise Diastereoselective Total Synthesis of α-Ambrinol.
Josefa L López-MartínezIrene Torres-GarcíaIrene Moreno-GutiérrezPascual Oña-BurgosAntonio Rosales MartínezManuel Muñoz-DoradoMiriam Álvarez-CorralIgnacio Rodríguez-GarcíaPublished in: Marine drugs (2023)
(-)- 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 CpTiCl 2 , an organometallic compound prepared in situ by a CpTiCl 3 reduction with Mn.