Synthesis of (+/-)-vibralactone.
Reductive alkylation of methyl 2-methoxybenzoate with prenyl bromide and hydrolysis afforded methyl 6-oxo-1-prenyl-2-cyclohexenecarboxylate. Reduction of the ketone, hydrolysis, iodolactonization, ozonolysis, and intramolecular aldol reaction provided a spiro lactone cyclopentenal. Retro-iodolactonization with activated Zn, formation of the beta-lactone, and reduction of the aldehyde completed an efficient first synthesis of (+/-)-vibralactone. No protecting groups were used except for the novel use of an iodolactone to protect both the prenyl double bond and carboxylic acid.
Zhou
Quan
Q
Department of Chemistry MS 015, Brandeis University, Waltham, Massachusetts 02454-9110, USA.
Snider
Barry B
BB
D000478:Alkylation; D001487:Basidiomycota / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D007783:Lactones; C522315:vibralactone