A Divergent Synthesis of the Delta(13)-9-Isofurans

作者:Taber Douglass F*; Gu Peiming; Li Rui
来源:Journal of Organic Chemistry, 2009, 74(15): 5516-5522.
DOI:10.1021/jo900767x

摘要

A stereodivergent total synthesis of the Delta(13)-9-isofurans has been developed. The four core substituted tetrahydrofurans were prepared by the Sharpless asymmetric epoxidation and Sharpless asymmetric dihydroxylation followed by cascade cyclization. The relative configuration at C-8 was inverted by oxidation followed by immediate L-Selectride reduction. The relative configuration of the C-15 diastereomers was assigned by (S)-Binol/LAH/EtOH reduction of the corresponding enone. This synthesis of the Delta(13)-9-isofurans will provide sufficient material for further investigation of their biological activity.

  • 出版日期2009-8-7