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Prins Cyclization of Bis(silyl) Homoallylic Alcohols to Form 2,6-cis-Tetrahydropyrans Containing a Geometrically Defined Exocyclic Vinylsilane: Efficient Synthesis of Ring B of the Bryostatins

Authors

  • Ji Lu,

    1. Key laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu, 610041 (China)
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  • Prof. Dr. Zhenlei Song,

    Corresponding author
    1. Key laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu, 610041 (China)
    2. State Key Laboratory of Biotherapy, West China Hospital, Sichuan University, Chengdu, 610041(China)
    • Key laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu, 610041 (China)
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  • Yuebao Zhang,

    1. Key laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu, 610041 (China)
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  • Zubao Gan,

    1. Key laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu, 610041 (China)
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  • Hongze Li

    1. Key laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu, 610041 (China)
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  • We are grateful for the financial support from the National Natural Science Foundation of China (21172150, 21021001), the National Basic Research Program of China (973 Program, 2010CB833200), and Sichuan University (Distinguished Young Scientist Program, 2011SCU04A18).

Abstract

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Prins Charming: Prins cyclization of a bis(silyl) homoallylic alcohol with an aldehyde shows excellent cis and Z selectivity to form tetrahydropyrans containing a geometrically defined exocyclic vinylsilane. This reaction was used as the key step in the synthesis of ring B of the bryostatins.

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