Daphnipaxinin (3), the first known diamino daphnicyclidin-type alkaloid, isolated in 2004, contains several synthetically challenging structural features. These include a compact, hexacyclic core containing two fused seven-member rings, five stereogenic centers (one quaternary) and an unusual aminofulvene moiety. Studies directed toward the asymmetric total synthesis of this natural product are reported. Key steps in our approach include an aza-Cope-Mannich reaction of (Z)-trisubstituted olefin 1 to form the A and C rings along with the quaternary stereocenter, and a ring-closing metathesis reaction to form the D ring.

Synthetic studies directed toward daphnicyclidin-type natural products

243rd National Meeting (2012)

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