Studies towards an Enantioselective Total Synthesis of Sarain A: A Concise Asymmetric Construction of the Diazatricyclic Core

Authors

  • Rui-Feng Yang,

    1. Department of Chemistry and The Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005 (P. R. China), Fax: (+86) 592-2186400
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  • Prof. Dr. Pei-Qiang Huang

    1. Department of Chemistry and The Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005 (P. R. China), Fax: (+86) 592-2186400
    2. State Key Laboratory of Bioorganic and Natural Products Chemistry, 354 Fenglin Lu, Shanghai 200032 (P. R. China)
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Abstract

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A powerful chiral building block: A concise enantioselective synthesis of the diazatricyclic core of sarain A has been accomplished. The novel strategy relies upon the versatile chiral building block (R)-1 (see scheme), and features a tandem Horner–Wadsworth–Emmons–aza-Michael reaction, an intramolecular Michael reaction, and the diastereoconvergent formation of the third ring. Diazatricyclic core 2 possesses all of the necessary functionality for further elaboration into sarain A.

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