Chemistry of tricarbonyl hemiketals and application of Evans technology to the total synthesis of the immunosuppressant (-)-FK-506

Details of model studies probing the chemistry of the tricarbonyl region of FK-506 are presented, and their use in designing a successful route to this immunosuppressant is outlined. Applications of asymmetric oxazolidinone alkylation/aldol methodology to a convergent, highly flexible synthesis of t...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 112; no. 8; pp. 2998 - 3017
Main Authors Jones, Todd K, Reamer, Robert A, Desmond, Richard, Mills, Sander G
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 01.04.1990
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
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Summary:Details of model studies probing the chemistry of the tricarbonyl region of FK-506 are presented, and their use in designing a successful route to this immunosuppressant is outlined. Applications of asymmetric oxazolidinone alkylation/aldol methodology to a convergent, highly flexible synthesis of the C10-C18 fragment and to improvements in the preparation of the C20-C34 segment are also discussed.
Bibliography:istex:4196FDE62BA8FF0EBA97066FE7A9A3C19225BC67
ark:/67375/TPS-SG2GVT1W-2
ISSN:0002-7863
1520-5126
DOI:10.1021/ja00164a023