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Synthesis of D-(+)-Biotin through Selective Ring Closure of N-Acyliminium Silyl Enol Ethers

Authors

  • Marinus J. Moolenaar,

    1. Laboratory of Organic Chemistry, University of Amsterdam, Nieuwe Achtergracht 129, NL-1018 WS Amsterdam (The Netherlands), Telefax: Int. code + (20)525-5670
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  • Prof. Dr. W. Nico Speckamp,

    Corresponding author
    1. Laboratory of Organic Chemistry, University of Amsterdam, Nieuwe Achtergracht 129, NL-1018 WS Amsterdam (The Netherlands), Telefax: Int. code + (20)525-5670
    • Laboratory of Organic Chemistry, University of Amsterdam, Nieuwe Achtergracht 129, NL-1018 WS Amsterdam (The Netherlands), Telefax: Int. code + (20)525-5670
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  • Dr. Henk Hiemstra,

    1. Laboratory of Organic Chemistry, University of Amsterdam, Nieuwe Achtergracht 129, NL-1018 WS Amsterdam (The Netherlands), Telefax: Int. code + (20)525-5670
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  • Dr. Eike Poetsch,

    1. E. Merck, Darmstadt (Germany)
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  • Dr. Michael Casutt

    1. E. Merck, Darmstadt (Germany)
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  • We thank J. R. Frowijn for his experimental work.

Abstract

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Irrespective of the geometry of the double bond the configuration of the newly formed chiral center is established by the existing adjacent stereogenic center in the Lewis acid catalyzed cyclization of the N-acyliminium silyl enol ether intermediate 1. This step is the key transformation in a new, concise total synthesis of D-( + )-biotin. R [DOUBLE BOND] protecting group.

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