The recognition of latent symmetry in the backbone of the F ring of the highly cytotoxic macrolide spongistatin 1 has allowed the development of a facile synthesis of the 6 contiguous stereocenters of the F ring fragment in 7 steps.  The analysis and route will be described, and when concatenated to the new chemistry being developed for the ABCD ring fragment, this chemistry will facilitate the construction of analogues and the development of an SAR around these fascinating anticancer agents.

Exploiting latent symmetry in a synthesis of spongistatins

243rd National Meeting (2012)

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