Assessing synthetic strategies: total syntheses of (+/-)-neodolabellane-type diterpenoids.
Two strategies, namely a cross-metathesis/ring-closing metathesis and Pd-catalyzed Stille allylation/Nozaki-Hiyama-Kishi coupling, are examined for the preparation of neodolabellane-type diterpenoids 1 and 2. Whereas the first approach possessed synthetic limitations, the latter was successfully employed to provide compounds 1 and 2 in 8.8% (14 steps) and 8% (15 steps) overall yields, respectively.
Valente
Cory
C
Department of Chemistry, York University, 4700 Keele Street, Toronto, ON, M3J 1P3, Canada.
Organ
Michael G
MG
D000478:Alkylation; D002384:Catalysis; D003500:Cyclization; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry; D013237:Stereoisomerism
D004224:Diterpenes; C533575:neodolabellane; D010165:Palladium