A new synthesis of (−)-thioambrox and its 8-epimer |
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| Authors: | Maria do Céu Costa Susana G Teixeira Cristina B Rodrigues Pedro Ryberg Figueiredo Maria João Marcelo Curto |
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| Institution: | Instituto Nacional de Engenharia, Tecnologia e Inovação (INETI), Departamento de Tecnologia das Indústrias Químicas, Estrada do Paço do Lumiar 1649-038 Lisboa, Portugal |
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| Abstract: | This new and straightforward synthesis of (−)-thioambrox 2, a sulphur compound whose odour resembles ambergris, starts from sclareolide 4. The stereoselectivity of the final cyclization is independent of the catalyst selected, and compound 2 is always favoured over (+)-iso-thioambrox 3. With hydrochloric acid as catalyst, the cyclization is unexpectedly stereospecific to give 2 in high yield at room temperature. |
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| Keywords: | Thioambrox iso-Thioambrox Stereoselective cyclization |
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