Synthesis of the norjatrophane diterpene (-)-15-acetyl-3-propionyl- 17-norcharaciol.
[reaction: see text] 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.
Helmboldt
Hannes
H
Fachrichtung Chemie, Technische Universität Dresden, D-01062 Dresden, Germany.
Köhler
Daniel
D
Hiersemann
Martin
M
D000475:Alkenes / Q000737:chemistry*; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
C516000:15-acetyl-3-propionyl-17-norcharaciol; D000475:Alkenes; D004224:Diterpenes