UC Berkeley

The total synthesis and synthetic efforts towards several diterpene natural products are described. The syntheses of the furanocembranoids coralloidolide B and coralloidolide C were both achieved in a single step from coralloidolide E. The furanocembranoid bipinnatin J was used in a model system to explore the conditions necessary to effect a transannular [2+2] cycloaddition in assembling the pentacyclic core of bielschowskysin. Two distinct strategies were evaluated as part of this model system for their effectiveness in synthesizing the cyclobutane ring of bielschowskysin. Progress was also made towards synthesizing a macrocyclic precursor of bielschowskysin. Numerous selective oxidations of the furanocembranoid carbon framework were discovered which should find utility in the synthesis of other members of this family of diterpenes. Several novel transformations of furanocembranoid derivatives are described, along with a synthesis of the furanocembranoid intricarene through photochemical means.