Marine Drugs
(Apr 2023)
A Concise Diastereoselective Total Synthesis of α-Ambrinol
Josefa L. López-Martínez,
Irene Torres-García,
Irene Moreno-Gutiérrez,
Pascual Oña-Burgos,
Antonio Rosales Martínez,
Manuel Muñoz-Dorado,
Míriam Álvarez-Corral,
Ignacio Rodríguez-García
Affiliations
Josefa L. López-Martínez
Organic Chemistry, University of Almería, CIAIMBITAL, 04120 Almería, Spain
Irene Torres-García
Organic Chemistry, University of Almería, CIAIMBITAL, 04120 Almería, Spain
Irene Moreno-Gutiérrez
Organic Chemistry, University of Almería, CIAIMBITAL, 04120 Almería, Spain
Pascual Oña-Burgos
Instituto de Tecnología Química, Universitat Politècnica de València-Consejo Superior de Investigaciones Científicas (UPV-CSIC), 46022 Valencia, Spain
Antonio Rosales Martínez
Department of Chemical Engineering, Escuela Politécnica Superior, University of Sevilla, 41011 Sevilla, Spain
Manuel Muñoz-Dorado
Organic Chemistry, University of Almería, CIAIMBITAL, 04120 Almería, Spain
Míriam Álvarez-Corral
Organic Chemistry, University of Almería, CIAIMBITAL, 04120 Almería, Spain
Ignacio Rodríguez-García
Organic Chemistry, University of Almería, CIAIMBITAL, 04120 Almería, Spain
DOI
https://doi.org/10.3390/md21040230
Journal volume & issue
Vol. 21,
no. 4
Abstract
Read online
(−)-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
WeChat QR code
Close
