Highly diastereoselective formation of spirocyclic compounds via 1,5-hydrogen transfer: a total synthesis of (-)-erythrodiene |
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Authors: | Lachia Mathilde Dénès Fabrice Beaufils Florent Renaud Philippe |
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Affiliation: | Departement für Chemie und Biochemie, Universit?t Bern, Freiestrasse 3, 3012 Bern, Switzerland. |
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Abstract: | [reaction: see text] A highly stereoselective synthesis of (-)-erythrodiene starting from 4-isopropylcyclohexanone is described. The key reactions are an asymmetric methoxycarbonylation of the starting ketone and a highly diastereoselective radical cascade involving addition of a phenylthiyl radical to a terminal alkyne followed by a 1,5-hydrogen transfer and a 5-exo-cyclization. |
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