Abstract

AbstractA sequence of vinylalumination of α‐substituted aldehydes, ring‐closing metathesis (RCM), and palladium‐catalyzed allylic substitution was utilized to prepare the biologically active natural products, pericosines, from d‐ribose. The anti‐adduct of vinylalumination was transformed into pericosine A after RCM, removal of the 4‐methoxybenzyl protecting group, and chlorination. The diacetate of the anti‐adduct was converted to pericosine C after the palladium‐catalyzed, SN2′‐type, allylic substitution. However, an unexpected dimeric product was generated in utilizing this approach to prepare pericosine E.

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