Utilization of molybdenum- and palladium-catayzed dynamic kinetic asymmetric transformations for the preparation of tertiary and quaternary stereogenic centers: a concise synthesis of tipranavir

Barry M Trost; Neil G Andersen

doi:10.1021/ja028497v

Utilization of molybdenum- and palladium-catayzed dynamic kinetic asymmetric transformations for the preparation of tertiary and quaternary stereogenic centers: a concise synthesis of tipranavir

J Am Chem Soc. 2002 Dec 4;124(48):14320-1. doi: 10.1021/ja028497v.

Authors

Barry M Trost¹, Neil G Andersen

Affiliation

¹ Department of Chemistry, Stanford University, Stanford, California 94305-5080, USA. bmtrost@stanford.edu

PMID: 12452702
DOI: 10.1021/ja028497v

Abstract

Tipranavir, an important antiviral agent in clinical development for the treatment of HIV, is synthesized in 15 linear steps from readily available starting materials in 25% overall yield by utilizing Pd- and Mo-catalyzed DYKAT reactions to control the quaternary and tertiary stereogenic centers, respectively.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, P.H.S.

MeSH terms

Catalysis
HIV Protease Inhibitors / chemical synthesis*
Kinetics
Molybdenum / chemistry*
Palladium / chemistry*
Pyridines / chemical synthesis*
Pyrones / chemical synthesis*
Stereoisomerism
Sulfonamides

Substances

HIV Protease Inhibitors
Pyridines
Pyrones
Sulfonamides
Palladium
Molybdenum
tipranavir

Grants and funding

GM 33049/GM/NIGMS NIH HHS/United States