Alotaketal A is a structurally unprecedented sesterterpenoids, isolated from the marine sponge Hamigera sp. by Andersen et al in 2009.1 Alotaketal A exhibits a range of useful bioactivities including potent activation of the cAMP signalling pathway in HEK293 cells (EC50= 18 nM). Given the importance of cAMP signaling to cellular function, alotaketal A represents a useful small molecule lead to further drug development as well as a potentially important probe for cell biology research.This poster describes the convergent total synthesis of (-)-alotaketal A, exploiting a remarkable LiDBB-mediated coupling of a (R)-carvone-derived d-lactone with an allyl bromide sidechain, followed by spiroacetalisation.2

Total synthesis of alotaketal A

245th National Meeting (2013)

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