The synthesis of the C(18)-C(34) fragment of amphidinolide C has been achieved via two routes, culminating in both the shortest (11 steps) and highest yielding (26% overall yield) approaches to this segment.  The highly convergent approach will facilitate the synthesis of analogues, including the C(18)-C(29) fragment of amphidinolide F. Synthetic highlights include the selective methylation of a diyne, and the highly efficient use of a second generation cobalt catalyst in the Mukaiyama oxidative cyclization to form the trans-THF ring.  A first generation route to the C(10)-C(17) fragment will also be discussed.

Studies toward the total synthesis of amphidinolide C. Part I: Synthesis of the C(18)-C(34) and C(10-C(17) fragments of amphidinolide C

244th National Meeting (2012)

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