Scalable Synthesis of the Potent HIV Inhibitor BMS‐986001 by Non‐Enzymatic Dynamic Kinetic Asymmetric Transformation (DYKAT) | Zendy

Ortiz Adrian | Zendy; Benkovics Tamas | Zendy; Beutner Gregory L. | Zendy; Shi Zhongping | Zendy; Bultman Michael | Zendy; Nye Jeffrey | Zendy; Sfouggatakis Chris | Zendy; Kronenthal David R. | Zendy

Premium

Scalable Synthesis of the Potent HIV Inhibitor BMS‐986001 by Non‐Enzymatic Dynamic Kinetic Asymmetric Transformation (DYKAT)

Author(s) -

Ortiz Adrian,

Benkovics Tamas,

Beutner Gregory L.,

Shi Zhongping,

Bultman Michael,

Nye Jeffrey,

Sfouggatakis Chris,

Kronenthal David R.

Publication year - 2015

Publication title -

angewandte chemie

Language(s) - English

Resource type - Journals

eISSN - 1521-3757

pISSN - 0044-8249

DOI - 10.1002/ange.201502290

Subject(s) - enantiopure drug , kinetic resolution , chemistry , combinatorial chemistry , furanose , pyranose , stereoselectivity , tautomer , transformation (genetics) , stereochemistry , ring (chemistry) , enantioselective synthesis , organic chemistry , catalysis , biochemistry , gene

Described herein is the synthesis of BMS‐986001 by employing two novel organocatalytic transformations: 1) a highly selective pyranose to furanose ring tautomerization to access an advanced intermediate, and 2) an unprecedented small‐molecule‐mediated dynamic kinetic resolution to access a variety of enantiopure pyranones, one of which served as a versatile building block for the multigram, stereoselective, and chromatography‐free synthesis of BMS‐986001. The synthesis required five chemical transformations and resulted in a 44 % overall yield.

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here

Accelerating Research