Synthesis of (±)-Bipinnatin J

Significance

Pseudopterogorgia Octocorals are a fruitful source of furanocembranoid natural products. The Bipinnatin subclass possesses members with potent anticancer and neurotoxic properties. One of the simplest members, (±)-Bipinnatin J, is of interest to investigate biosynthetic routes to other Bipinnatins and related furanocembranoids. Of interest in this synthesis are (1) the Negishi cross-coupling with which to prepare C and (2) the intramolecular diastereoselective Nozaki-Hiyama-Kishi reaction of D to (±)-Bipinnatin J.