Enantioselective Synthesis of the ABC-Tricyclic Core of Phomactin A by a γ‑Hydroxylation Strategy

Abstract

An enantioselective synthesis of the ABC-tricyclic furanochroman core of phomactin A has been accomplished by a γ-hydroxylation approach. The C ring was established by γ-hydroxylation of an α-enone. The regioselectivity was optimized by using a strong base with an oxophilic cation (<i>t-</i>BuLi) and a bulky oxygen donor (Davis reagent), which afforded the γ-hydroxylation product selectively in 63% yield