ePrints

Judicious application of allyl protecting groups for the synthesis of 2-morpholin-4-yl-4-oxo-4H-chromen-8-yl triflate, a key precursor of DNA-dependent protein kinase inhibitors

Lookup NU author(s): Emeritus Professor Bernard Golding, Professor Roger Griffin, Dr Ian HardcastleORCiD

Downloads

Full text for this publication is not currently held within this repository. Alternative links are provided below where available.

Abstract

2- Morpholin4-yl-4-oxo-4H-chromen-8-yl2,2,2-trifluoromethanesulfonate is a key intermediate for the synthesis of the DNA-dependent protein kinase (DNA-PK) inhibitor 8-dibenzothiophen-4-yl-2-morpholin-4-yl-chromen-4-one(NU7441). Two improved methods for the synthesis of this triflate have been developed: (A) in 35% overall yield, through modification of the published route, and ( B) in 15% overall yield, by a new route employing a Baker - Venkataraman rearrangement to enable generation of the chromenone scaffold. Both syntheses depend on the judicious use of allyl protecting groups.

Publication metadata

Author(s): Aristegui SR, El-Murr MD, Golding BT, Griffin RJ, Hardcastle IR

Publication type: Article

Publication status: Published

Journal: Organic Letters

Year: 2006

Volume: 8

Issue: 26

Pages: 5927-5929

Date deposited: 12/05/2010

ISSN (print): 1523-7060

ISSN (electronic): 1523-7052

URL: http://dx.doi.org/10.1021/ol062297x

DOI: 10.1021/ol062297x

PubMed id: 17165896

Altmetrics

Share