Unknown

Dataset Information

0

Formal synthesis of (+)-brefeldin A: application of a zinc-mediated ring expansion reaction.


ABSTRACT: An efficient formal synthesis of (+)-brefeldin A was accomplished through a synthetic approach that relied upon three keys steps. The five-membered ring was generated in a stereocontrolled fashion through application of a tandem conjugate addition-intramolecular cyclization method developed by Toru. Ring-closing metathesis provided access to a twelve-membered beta-keto lactone, which was ring-expanded to the alpha,beta-unsaturated-gamma-keto lactone through a zinc carbenoid-mediated reaction. Conversion of this lactone to (+)-brefeldin A has been reported previously.

SUBMITTER: Lin W 

PROVIDER: S-EPMC2572133 | biostudies-literature | 2007 Jun

REPOSITORIES: biostudies-literature

altmetric image

Publications

Formal synthesis of (+)-brefeldin A: application of a zinc-mediated ring expansion reaction.

Lin Weimin W   Zercher Charles K CK  

The Journal of organic chemistry 20070512 12


An efficient formal synthesis of (+)-brefeldin A was accomplished through a synthetic approach that relied upon three keys steps. The five-membered ring was generated in a stereocontrolled fashion through application of a tandem conjugate addition-intramolecular cyclization method developed by Toru. Ring-closing metathesis provided access to a twelve-membered beta-keto lactone, which was ring-expanded to the alpha,beta-unsaturated-gamma-keto lactone through a zinc carbenoid-mediated reaction. Co  ...[more]

Similar Datasets

| S-EPMC2715010 | biostudies-literature
| S-EPMC6242278 | biostudies-literature
| S-EPMC6115638 | biostudies-literature
| S-EPMC6423569 | biostudies-literature
| S-EPMC4471581 | biostudies-literature
| S-EPMC3062847 | biostudies-literature
| S-EPMC4661008 | biostudies-literature
| S-EPMC4955225 | biostudies-literature
| S-EPMC3222144 | biostudies-literature
| S-EPMC10996026 | biostudies-literature