Unknown

Dataset Information

0

Total synthesis of the potent androgen receptor antagonist (-)-arabilin: a strategic, biomimetic [1,7]-hydrogen shift.


ABSTRACT: The first total synthesis of (-)-arabilin, a Streptomyces metabolite that inhibits hormone activation of the androgen receptor, has been completed. The key step, a [1,7]-hydrogen shift, establishes the enol ether-containing skipped-tetraene substructure. This nonenzymatic pericyclic reaction is considered to be biomimetic.

SUBMITTER: Lim HN 

PROVIDER: S-EPMC3320024 | biostudies-literature | 2011 Dec

REPOSITORIES: biostudies-literature

altmetric image

Publications

Total synthesis of the potent androgen receptor antagonist (-)-arabilin: a strategic, biomimetic [1,7]-hydrogen shift.

Lim Hee Nam HN   Parker Kathlyn A KA  

Journal of the American Chemical Society 20111129 50


The first total synthesis of (-)-arabilin, a Streptomyces metabolite that inhibits hormone activation of the androgen receptor, has been completed. The key step, a [1,7]-hydrogen shift, establishes the enol ether-containing skipped-tetraene substructure. This nonenzymatic pericyclic reaction is considered to be biomimetic. ...[more]

Similar Datasets

| S-EPMC8457242 | biostudies-literature
| S-EPMC2837585 | biostudies-literature
| S-EPMC4944760 | biostudies-literature
| S-EPMC6766977 | biostudies-literature
| S-EPMC3985950 | biostudies-literature
| S-EPMC5718057 | biostudies-literature
| S-EPMC2750869 | biostudies-literature
| S-EPMC4284651 | biostudies-literature
| S-EPMC3204860 | biostudies-literature
| S-EPMC6994261 | biostudies-literature