Synthetic Approaches to Rapamycin: Synthesis of a C10-C26 Fragment via a One-Pot Julia Olefination Reaction
- 1 February 1996
- journal article
- research article
- Published by Georg Thieme Verlag KG in Synthesis
- Vol. 1996 (02) , 285-296
- https://doi.org/10.1055/s-1996-4184
Abstract
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.Keywords
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