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Synlett 1999; 1999(3): 295-298
DOI: 10.1055/s-1999-2607
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Synthetic Studies Towards the B,C,D,E Fragment of Antibiotic CP44, 161

Paul A. Allen* , Margaret A. Brimble, Hishani Prabaharan
  • *Department of Chemistry, University of Auckland, Private Bag 90219, Auckland, New Zealand
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Publication Date:
31 December 1999 (online)

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The synthesis of polyethers 32 and 33 from tricyclic bis-spiroacetal aldehyde 27 and E-bromide 7 are described. A key step in the synthetic strategy involved the oxidative cyclisation of a bicyclic hydroxyspiroacetal 22a,b to a cis bis-spiroacetal unit, which resulted in preferential formation of cis aldehyde 27. A Barbier reaction of bromide 7 and tricyclic aldehyde 27 then afforded erythro alcohol 28 which after epoxidation and acid catalysed cyclisation completed the synthesis of polyethers 32 and 33 providing an effective framework on which to synthesise the B,C,D and E rings of antibiotic CP44,161 1.

bis-spiroacetal - polyether - oxidative cyclisation