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Synthesis 1996; 1996(2): 285-296
DOI: 10.1055/s-1996-4184
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Synthetic Approaches to Rapamycin: Synthesis of a C10-C26 Fragment via a One-Pot Julia Olefination Reaction

Richard Bellingham, Krzysztof Jarowicki, Philip Kocienski* , Valerie Martin
  • *Department of Chemistry, The University, Southampton, SO17 1BJ, UK, Fax +44(1703)593781; E-mail PJK1@soton.ac.uk
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Publication Date:
31 December 2000 (online)

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Key steps in a synthesis of the C10-C26 fragment of the immunosuppressant Rapamycin include (a) the use of a metallated benzothiazolyl sulfone in a one-pot Julia olefination to create the C21-C22 alkene stereoselectively and (b) a diastereoselective acid-catalysed cyclisation of a hydroxyl function onto a ketenedithioacetal (1,4-asymmetric induction) in order to create the oxane ring and fix the stereochemistry at C11.

rapamycin - immunosuppressant - ketenedithioacetal - triene 1,4-asymmetric induction - Julia olefination