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DOI: 10.1055/s-2008-1077982
Synthesis of (±)-Vibralactone
Contributor(s):Philip Kocienski, Indu DagerBrandeis University, Waltham, USA
Synthesis of (±)-Vibralactone
Org. Lett. 2008, 10: 1401-1404
Publication History
Publication Date:
22 August 2008 (online)
Key words
(±)-vibralactone - aldol reaction - Birch reduction - β-lactones
Significance
(±)-Vibralactone is isolated from cultures of the Basidiomycete Boreostereum vibrans. It is a pancreatic lipase inhibitor which could be used for the treatment of obesity. The first synthesis of (±)-vibralactone depicted here involves an intramolecular aldol reaction of a dialdehyde derived by ozonolysis of E to afford the cyclopentenal F.
Comment
Reduction of ketone C to the desired alcohol proved to be a difficult step. After trying many different methods, reduction was finally achieved with Me4NBH4 to afford the cis-alcohol D in 42% yield along with 40% of mixtures of cis and trans diastereoisomers. Note the use of an iodolactone for the internal protection of the alkene (D → E).