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A Concise Diastereoselective Total Synthesis of α-Ambrinol.

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.

SUBMITTER: Lopez-Martinez JL

PROVIDER: S-EPMC10145093 | biostudies-literature | 2023 Apr

REPOSITORIES: biostudies-literature

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A Concise Diastereoselective Total Synthesis of α-Ambrinol.

López-Martínez Josefa L JL Torres-García Irene I Moreno-Gutiérrez Irene I Oña-Burgos Pascual P Rosales Martínez Antonio A Muñoz-Dorado Manuel M Álvarez-Corral Míriam M Rodríguez-García Ignacio I

Marine drugs 20230401 4

(-)-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. ...[more]

PMID: 37103369

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