Total Synthesis of Spirastrellolide A Methyl Ester—Part 1: Synthesis of an Advanced C17–C40 Bis-spiroacetal Subunit

Authors


  • This work was supported by the EPSRC (GR/C541677/1), Merck Research Laboratories, Homerton College, Cambridge (E.A.A.), SK Corporation (J.H.L.), and the German Academic Exchange Service (C.M.). We thank Prof. R. J. Andersen (University of British Columbia) for helpful discussions.

Abstract

original image

Out of the blue: The marine macrolide spirastrellolide A is a potent and selective inhibitor of protein phosphatase 2A and a lead for anticancer therapies. A flexible and modular synthetic strategy has been developed with two routes for the construction of the DEF bis-spiroacetal subunit. The optimized Suzuki coupling approach results in the efficient preparation of a C17–C40 aldehyde that forms the cornerstone of the first total synthesis.

Ancillary