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Domino access to highly substituted chromans and isochromans from carbohydrates


Herein we describe the synthesis of highly substituted chromans and isochromans using carbohydrates as starting materials. Our approach makes use of a Pd-catalyzed domino reaction consisting of oxidative addition, followed by two carbopalladation steps and completed by a cyclization to annelate the benzene moiety. The versatility of this route has been demonstrated by a small library of highly substituted chromans and isochromans.

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We are grateful to the Deutsche Forschungsgemeinschaft and the Fonds der Chemischen Industrie for financial support (Emmy Noether Fellowship and Liebig Fellowship to D.B.W.). D.C.K. thanks the Studienstiftung des deutschen Volkes for his undergraduate fellowship and the Fonds der Chemischen Industrie for his PhD fellowship. S.C.S. acknowledges the Konrad-Adenauer-Stiftung for her undergraduate fellowship. We thank L.F. Tietze (University of Göttingen) for helpful discussions and generous support of our work.

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D.B.W. designed the project. M.L., D.C.K., M.P. and S.C.S. performed the experiments. The manuscript was written by D.B.W.

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Correspondence to Daniel B Werz.

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The authors declare no competing financial interests.

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Leibeling, M., Koester, D., Pawliczek, M. et al. Domino access to highly substituted chromans and isochromans from carbohydrates. Nat Chem Biol 6, 199–201 (2010).

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