A Second-Generation Total Synthesis of Spirastrellolide A Methyl Ester


  • This work was supported by the EPSRC, Clare College, Cambridge (S.M.D.), Homerton College, Cambridge (E.A.A.), and SK Innovation (J.H.L.). We thank Dr. Julien Genovino (Cambridge) for valuable experimental contributions, and the EPSRC national mass spectrometry service (Swansea) for mass spectra.


original image

Marine macrolides: An improved second-generation total synthesis of the anticancer macrolide spirastrellolide A methyl ester has been achieved. The synthesis features a uniformly high level of stereocontrol combined with more expedient fragment assembly, and demonstrates a critical dependence of the crucial macrolactonization step on the substitution pattern of the C22–C24 linker region.