Synthesis of epothilones

US6211412A · kind A · utility

Assignee

• University of Kansas · US

Inventors

• Gunda I. Georg · Minneapolis, US
• Sajiv K. Nair · Lawrence, US
• Emily Reiff · Lawrence, US
• Ashok Rao Tunoori · Lawrence, US
• John T. Henri · Longmont, US

Key dates

• Filing date: Mar 29, 1999
• Grant date: Apr 3, 2001
• Expiry date: Mar 29, 2019

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07B2200/07
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

Commercially feasible methods for synthesizing various epothilones precursors needed for the preparation of final epothilones are provided, including techniques for the synthesis of epothilone segment C using a stereoselective Noyori-type reduction, and the coupling of epothilone segments B and C using an aldol condensation reaction. The synthesis methods may be used to prepare naturally occurring segments as well as a large number of related analogs and homologs thereof. Final epothilones in accordance with the invention may also be of the naturally occurring variety (16-membered macrolides), while the homologs and analogs thereof are preferably up to 20-membered macrolides.