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Enantioselective Construction of Pyrroloindolines Catalyzed by Chiral Phosphoric Acids: Total Synthesis of (−)-Debromoflustramine B

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  • We thank the National Institutes of Health (NIH GM-082935) and the National Science Foundation CAREER program (NSF-0847108) for financial support.

Abstract

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Acids in command: The asymmetric formation of pyrroloindolines with adjacent quaternary and tertiary carbon centers has been achieved through catalysis by a chiral phosphoric acid. Starting from readily available tryptamine, both Michael products and amination products were obtained in high yields and enantioselectivities. The significance of this study was further demonstrated by the total synthesis of (−)-debromoflustramine B.

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