A Failed Late-Stage Epimerization Thwarts an Approach to Ineleganolide

作者:Horn Evan J; Silverston Joel S; Vanderwal Christopher D*
来源:Journal of Organic Chemistry, 2016, 81(5): 1819-1838.
DOI:10.1021/acs.joc.5b02550

摘要

Significant efforts were made to complete a synthesis of the complex norcembranoid ineleganolide via a seemingly attractive strategy involving late-stage creation of the central seven-membered ring. While the two key enantioenriched building blocks were made via high-yielding sequences and their convergent union was efficient, the critical C4-C5 bond of this sterically congested natural product could never be forged. Several interesting examples of unexpected acid-base behavior and unanticipated proximity-induced reactivity accounted for most of the problems in the execution of the synthesis plan.

  • 出版日期2016-3-4