Gonytolide A is a dimeric chromanone natural product isolated from the fungus <i>Gonytrichum</i> sp. along with its likely biogenetic precursor gonytolide C. Gonytolide A is an interesting synthetic target because it possesses a very crowded biaryl axis and exhibits excellent innate immune-promoting activity. We describe herein an asymmetric CuH reduction-enabled kinetic resolution of of (±)-chromone butenolide to afford (+)-gonytolide C, an asymmetric bromination-enabled kinetic resolution of a (±)-gonytolide C, and an atropselective oxidative coupling of (+)-bromo-gonytolide C to afford (+)-gonytolide A and its atropisomer.

Asymmetric synthesis of gonytolide A

256th National Meeting (2018)

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