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Synthesis of the Norjatrophane Diterpene (−)-15-Acetyl-3-propionyl- 17-norcharaciol

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journal contribution
posted on 2006-04-13, 00:00 authored by Hannes Helmboldt, Daniel Köhler, Martin Hiersemann
A scalable enantioselective synthesis of the nonnatural 17-norjatrophane diterpene 3-propionyl-15-acetyl-17-norcharaciol is described. Key C/C-connecting transformations are an Evans aldol reaction, an intramolecular carbonyl ene reaction, a Horner−Wadsworth−Emmons olefination, and a ring-closing metathesis for the formation of a 12-membered carbacycle.