title: A Failed Late-Stage Epimerization Thwarts an Approach to Ineleganolide.
abstract: 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.
authors: Department of Chemistry, University of California , 1102 Natural Sciences II, Irvine, California 92697-2025, United States.
authors: Evan J
authors: EJ
authors: Horn
authors: Department of Chemistry, University of California , 1102 Natural Sciences II, Irvine, California 92697-2025, United States.
authors: Joel S
authors: JS
authors: Silverston
authors: Department of Chemistry, University of California , 1102 Natural Sciences II, Irvine, California 92697-2025, United States.
authors: Christopher D
authors: CD
authors: Vanderwal