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Total Synthesis of Antascomicin B

Authors


  • The authors would like to thank Novartis for the Novartis Research Fellowship (to S.V.L.), Trinity College, Cambridge for a Junior Research Fellowship (to D.E.A.B.), Pembroke College, Cambridge and the Royal Society for fellowships (to M.D.S.), the EPSRC (to C.M.G.-J., M.R.L., C.M., and D.E.A.B.), Tanabe Seiyaku Co., Ltd. for a postdoctoral fellowship (to K.Y.), and the Japanese Society for the Promotion of Sciences (to R.A.). The authors would also like to acknowledge the contribution of Prof. Hidenori Watanabe (University of Tokyo; Cambridge 1998–2000) whose studies on a related system were invaluable in the development of the macrocyclization method described herein.

Abstract

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Das strukturell bestechende Antascomicin B (1), das ein starker Immunsuppressiva-Antagonist ist, hat eine komplexe Polyketidstruktur. Zu den Schlüsselschritten seiner enantioselektiven Totalsynthese gehören eine transannulare Catechol-gestützte Dieckmann-Reaktion, um die anspruchsvolle Tricarbonylfunktionalität zu erhalten, und eine Butandiacetal-gesteuerte Allylierung.

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