Total synthesis of (+)-fastigiatine.
The first total synthesis of the Lycopodium alkaloid (+)-fastigiatine has been accomplished in 15 steps and 30% overall yield from known compounds. Noteworthy transformations include a convergent fragment coupling via a nucleophilic cyclopropane opening, a highly diastereoselective formal [3 + 3]-cycloaddition, and a transannular Mannich reaction to construct the core of the natural product.
Liau
Brian B
BB
Department of Chemistry & Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA.
Shair
Matthew D
MD
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D032502:Lycopodium / Q000737:chemistry*; D013237:Stereoisomerism
D000470:Alkaloids; C553375:fastigiatine