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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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Präparativ nützlich: Die Prins-Cyclisierung eines Bis(silyl)homoallylalkohols mit einem Aldehyd führt mit exzellenter cis- und Z-Selektivität zu Tetrahydropyranen, die ein geometrisch definiertes exocyclisches Vinylsilan enthalten. Die Reaktion diente als Schlüsselschritt in der Synthese von Ring B der Bryostatine.

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