Total Synthesis of (±)-Epoxysorbicillinol

Keywords

(±)-epoxysorbicillinol - genus trichoderma - vertinoid polyketides - diazotization - 1,3-dipolar cycloaddition - Weitz–Scheffer epoxidation

Significance

Wood and co-workers reported the first total synthesis of (±)-epoxysorbicillinol in 2001. Isolated as the first vertinoid polyketide with an epoxide, the core skeleton was constructed via 1,3-dipolar cycloaddition to synthesize a diastereomerically pure oxabicycle. Selection of the diester malonate and later transesterification proved to be vital in preventing any unwanted aromatic side products in accessing the oxabicyclic ring.

 

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Comment

Diketone C was condensed with hydrazine D followed by treatment with basic alumina to give diazo E. 1,3-Dipolar cycloaddition with allyl propiolate F then furnished oxabicycle G. Deprotection of the allyl ester followed by amide formation gave Weinreb amide I. Addition of lithiated J gave ketone K, which then underwent Weitz–Scheffer epoxidation to yield epoxy alcohol L. Treatment with TFA gave facile access to enol M. The desired diene was accessed by DDQ oxidation to ultimately synthesize (±)-epoxysorbicillinol.

 

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Publikationsverlauf

Artikel online veröffentlicht:
23. Juli 2025