Lewis Acid Catalyzed Formal Intramolecular [3+2] Cross-Cycloaddition of Cyclopropane 1,1-Diesters with Alkenes: General and Efficient Strategy for Construction of Bridged [n.2.1] Carbocyclic Skeletons

Authors

  • Dr. Wenju Zhu,

    1. State Key Laboratory of Elemento-Organic Chemistry Institute of Elemento-Organic Chemistry, Nankai University, 94# Weijin Road, Tianjin 300071 (P.R. China)
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  • Jie Fang,

    1. State Key Laboratory of Elemento-Organic Chemistry Institute of Elemento-Organic Chemistry, Nankai University, 94# Weijin Road, Tianjin 300071 (P.R. China)
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  • Yong Liu,

    1. State Key Laboratory of Elemento-Organic Chemistry Institute of Elemento-Organic Chemistry, Nankai University, 94# Weijin Road, Tianjin 300071 (P.R. China)
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  • Jun Ren,

    1. State Key Laboratory of Elemento-Organic Chemistry Institute of Elemento-Organic Chemistry, Nankai University, 94# Weijin Road, Tianjin 300071 (P.R. China)
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  • Prof. Zhongwen Wang

    Corresponding author
    • State Key Laboratory of Elemento-Organic Chemistry Institute of Elemento-Organic Chemistry, Nankai University, 94# Weijin Road, Tianjin 300071 (P.R. China)
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  • We thank the NSFC (Nos 20972069, 21172109 and 21121002), MOST for 973 Project (No. 2010CB126106), and National Key Technologies R&D Program (2011BAE06B05) for financial support. We are indebted to Prof. Xianhe Bu and Mr. Suijun Liu for assistance with the single-crystal X-ray analysis, and thank Prof. Zhihong Wang and Prof. R. Brückner for useful suggestions regarding the NMR spectroscopy.

Abstract

original image

Carbon bridges: The title reaction has been successfully developed, and applied to the total synthesis of the tetracyclic diterpenoids phyllocladanol and phyllocladene. The method provides an efficient, general, and conceptually new strategy for the construction of structurally complex and diverse [n.2.1] carbocyclic skeletons (see scheme).

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