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Synlett 1996; 1996(9): 900-902
DOI: 10.1055/s-1996-5603
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Synthetic Approaches to Rapamycin. 2. A Synthesis of a C21-C42 Fragment

Mark Norley, Philip Kocienski* , Andrew Faller
  • *Department of Chemistry, The University, Southampton, SO17 1BJ, UK, FAX: 0044 1703 678825, 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 a C21-C42 fragment of rapamycin include a [3,3]-sigmatropic rearrangement to introduce the correct relative stereochemistry at C27 and C28 and the use of a furylsilane as a latent hydroxyl group at C28.

rapamycin - Fleming-Tamao oxidation - furan photooxidation - silylstannylation - Ireland-Claisen rearrangement