Simple designs for the construction of complex trans-fused polyether toxin frameworks. A linear strategy based on entropically favored oxirane ring enlargement in …

…, MT Diaz, R Perez, JL Ravelo, A Regueiro…

Index: Alvarez, Eleuterio; Diaz, Maria T.; Perez, Ricardo; Ravelo, Jose L.; Regueiro, Alicia; et al. Journal of Organic Chemistry, 1994 , vol. 59, # 10 p. 2848 - 2876

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Citation Number: 88

Abstract

A successful design for the construction of trans-fused medium-size cyclic ethers is described. The key features of the synthesis are as follows:(i) intramolecular oxirane ring expansion in cycloalkenes to give bridged oxabicyclic systems and (ii) linear, one-or two- directional synthetic operations which generate external oxocycles in single reaction steps. The general approach involves the intramolecular addition of a stable y-alkoxy-substituted ...