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Synlett 1994; 1994(2): 152-154
DOI: 10.1055/s-1994-22774
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Synthesis of Some Cephem Spiroacetal-Lactones

John H. Bateson* , George Burton, Susan A. Elsmere, Richard L. Elliott
  • *SmithKline Beecham Pharmaceuticals, Research Division, Brockham Park, Betchworth, Surrey, RH3 7AJ, UK
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Publication Date:
22 March 2002 (online)

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Reaction of the cephem-3-triflate 4 and of the 3-chloromethyl cephem 6 with tri-n-butyl (5,6-dihydropyran-2-yl)stannane 3 in the presence of catalytic quantities of Pd (dba)2 and tri(2-furyl)phosphine gave enol ethers 5 and 7, respectively. Exposure of 5 to TFA produced the spiroacetal-γ-lactones 9 and 10 in similar proportion, whereas deprotection of 7 afforded an isomer of the spiroacetal-δ-lactone 13 as the major product.