 Enigmazole A, isolated from Papua New Guinea marine sponge Cinachyrella enigmatica by K. Gustafson et al. in 2006 and displayed potent cytotoxic activity and as such comprises an interesting synthetic target. Central to the structure of the natural product is a pyran ring embedded within a 16-membered lactone, a substituted oxazole side chain, and a phosphate group.Highlight of our synthetic approach includes addition of an oxazole-substituted dithiane to an epoxide and a Petasis-Ferrier union/rearrangement of advanced aldehyde and hydroxyacid fragments to construct the cis-pyrane motif. Late stage Yamaguchi macrolactonization and introduction of the phosphate group is anticipated to complete the total synthesis.

Progress toward the total synthesis of enigmazole A

244th National Meeting (2012)

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