Synthesis of (+)-8-Deoxyvernolepin

Article abstract of DOI:10.1021/jo00100a049

A short and efficient synthesis of (+)-8-deoxyvernolepin (2) from (-)-α-santonin (8), by functionalization of the angular methyl from a 2β- or 6β-alkoxy radical generated by reaction of the alcohol 6 or 7 with diphenylhydroxyselenium acetate and iodine and 1,4-fragmentation of the γ-hydroxystannane 35 using hypervalent organoiodine reagents as the key steps, is described.The most important structural features of this compound and other vernolepin congeners, the δ-valerolactone cis-fused to ring B moiety and the angular vinyl group, are introduced in the same step.