Ontology highlight
ABSTRACT:
SUBMITTER: Angeles AR
PROVIDER: S-EPMC2646880 | biostudies-other | 2008 Oct
REPOSITORIES: biostudies-other
Journal of the American Chemical Society 20080911 41
A convergent, stereocontrolled route to either antipode of the cell adhesion inhibitor, peribysin E, has been achieved from carvone. Highlights of the synthesis include a Diels-Alder reaction to generate a cis-decalin framework, followed by semipinacol-type ring contraction to secure the stereochemistry of the C7 quaternary center. Potential mechanistic pathways for the critical ring contraction were studied through deuterium incorporation studies. In addition, an optimized olefin isomerization/ ...[more]