Biomimetic synthesis of fused bispyran: Lewis acid effects on oxacyclizations of polyepoxides

R Tong, FE McDonald, X Fang, KI Hardcastle

Index: Tong, Rongbiao; McDonald, Frank E.; Fang, Xikui; Hardcastle, Kenneth I. Synthesis, 2007 , # 15 p. 2337 - 2342

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Citation Number: 6

Abstract

Abstract The biomimetic synthesis of fused bispyran via Lewis acid mediated tandem oxacyclization of a 1, 4, 7-polyepoxide is explored. The nature of the Lewis acid promoter is critical for the endo-regioselectivity of epoxide cyclization, although anomalous apparent retention of stereochemistry is observed at some reactive centers.