Biomimetic Synthesis of Nor-Cedrene and Nor-Isozizaene Sesquiterpenoids and Exploration of Their Olfactive Properties |
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Authors: | Tony Georgiev Dr. Nicolas Armanino |
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Affiliation: | 1. Philochem AG, Libernstrasse 3, 8112 Otelfingen, Switzerland;2. Fragrance Discovery Research Givaudan Suisse SA, Kemptpark 50, 8310 Kemptthal, Switzerland |
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Abstract: | We report the preparation of nor-bisabolyl epoxide 13 and its use as a common biomimetic intermediate for the synthesis of nor-sesquiterpenoids. Through a cationic cyclization cascade pathway, we prepared nor-isozizaenol 25 , ultimately constituting an eight-step access to this complex sesquiterpenoid from inexpensive and abundant starting materials. Using a radical cyclization cascade pathway, we prepared nor-cedryl alcohol 26 from the same intermediate. Derivatization of these two products led to the discovery of two potent woody odorants of interest in perfumery. |
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Keywords: | biomimetic synthesis cationic cyclization fragrances radical cyclization terpenes |
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