A concise asymmetric, formal synthesis of (+)-hamigeran B is reported. A Pd-catalyzed, decarboxylative allylic alkylation, employing a trifluoromethylated derivative of t-BuPHOX, is utilized as the enantioselective step to form the critical quaternary carbon center in excellent yield and enantioselectivity. The product is converted in three steps to a late-stage intermediate previously used in the synthesis of hamigeran B.
Bibliographical noteKAUST Repository Item: Exported on 2020-10-01
Acknowledged KAUST grant number(s): K US-11-006-02
Acknowledgements: This publication is based on work supported by Award No. K US-11-006-02, made by King Abdullah University of Science and Technology (KAUST). Additionally, the authors wish to thank NIH-NIGMS (R01 GM 080269-01), Abbott Laboratories, Amgen, the Gordon and Betty Moore Foundation, and Caltech for financial support and Materia, Inc. for the kind donation of catalyst 8. Dr. Douglas C. Behenna is gratefully acknowledged for assistance in the preparation of the manuscript.
This publication acknowledges KAUST support, but has no KAUST affiliated authors.