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Total Synthesis of (−)-Rhizopodin


  • This work was supported by the EPSRC (J.G.-T.) and Clare College, Cambridge (S.M.D.). We thank the EPSRC National Mass Spectrometry Centre (Swansea) for mass spectra.


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Core assembly: The total synthesis of the myxobacterial metabolite rhizopodin, a potent actin-binding anticancer agent, has been achieved. The modular synthesis utilizes a common C1–C22 monomeric unit to assemble the dimeric 38-membered macrodiolide core, which was elaborated by a bidirectional boron-mediated aldol reaction to install the characteristic side-chains. The final global deprotection was critically dependent on the correct choice of silyl protecting groups at C16/C16′.