Synlett 2015; 26(01): 79-83
DOI: 10.1055/s-0034-1378614
letter
© Georg Thieme Verlag Stuttgart · New York

A Radical-Mediated Approach to the Total Synthesis of Fluorinated Marinoquinoline A and Related Tricyclic and Tetracyclic Congeners

Bhaven Patel
UCL School of Pharmacy, 29-39 Brunswick Square, London, WC1N 1AX, UK   Fax: +44(20)7535964   Email: s.hilton@ucl.ac.uk
,
Stephen T. Hilton*
UCL School of Pharmacy, 29-39 Brunswick Square, London, WC1N 1AX, UK   Fax: +44(20)7535964   Email: s.hilton@ucl.ac.uk
› Author Affiliations
Further Information

Publication History

Received: 09 June 2014

Accepted after revision: 15 July 2014

Publication Date:
07 October 2014 (online)


Abstract

A radical-mediated approach to the core structure of fluorinated marinoquinoline A, N-methylated marinoquinoline A and related congeners via the use of Togni’s reagent is described.

Supporting Information

 
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  • 22 General Procedure for Radical Cyclisation: A solution of isocyanide (1 equiv), TMAI (0.05 equiv) and Togni’s reagent (1.5 equiv) in 1,4-dioxane (0.2 M) was heated at 80 °C for 3 h. The residue was concentrated under reduced pressure and purified via Biotage to give the cyclised products. Full experimental details and characterisation data are available in the Supporting Information.