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Synlett 1994; 1994(1): 77-78
DOI: 10.1055/s-1994-22745
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A Synthetic Approach to the C26-C32 Fragment of Rapamycin. A Synthesis of Allylic Alcohols from Allylic Furylsilanes.

Mark C. Norley* , Philip J. Kocieński, Andrew Faller
  • *Department of Chemistry, The University, Southampton, SO9 5NH, U. K.
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Publication Date:
22 March 2002 (online)

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Key steps in a synthesis of the C23-C32 fragment of rapamycin include a regioselective Pd(0)-catalysed silylstannylation of an alkyne; a Pd(0)-catalysed coupling of a (Z)-2-silyl-1-stannylalkene with an acid choride; and a Fleming-Tamao oxidation of an allylic silanol generated by photo-oxidation of an allylic furyldimethylsilane.