Synthetic efforts towards the C1�C25 fragment of the polyketide natural product spirastrelolide B is reported.  Originally isolated in 2007, spirastrellolide B and its congeners possess interesting biological activity and feature a challenging framework including a 38-membered macrolactone, a bicyclic and a tricyclic spiroacetal subunit.  A strategy aimed at developing phosphate tether-mediated regio- and chemoselective reactions to facilitate the synthesis of the C1�C25 fragment in an efficient manner will be discussed.

Phosphate tether-mediated approach towards the C1�C25 fragment of Spirastrellolide B

248th National Meeting (2014)

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