Journal of Organic Chemistry p. 6395 - 6403 (1994)
Update date:2022-07-30
Topics:
Hernandez, Rosendo
Valazquez, Silvia M.
Suarez, Ernesto
Rodriguez, Maria S.
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.
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Doi:10.1080/00397919408010611
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