Stereocontrolled synthesis of C1-C17 fragment of narasin via a free radical-based approach.
An efficient synthesis of the C1-C17 western unit of narasin was achieved from (S)-Roche ester. Highlights in our synthesis include the successful exploitation of three stereoselective sequences of Lewis acid mediated reaction followed by free-radical-based hydrogen transfer.
Brazeau
Jean-François
JF
Institut de recherches cliniques de Montréal, Bio-organic Chemistry Laboratory, 110 avenue des Pins Ouest, Montréal, Québec, Canada H2W 1R7.
Guilbault
Audrey-Anne
AA
Kochuparampil
Jummey
J
Mochirian
Philippe
P
Guindon
Yvan
Y
D005609:Free Radicals / Q000737:chemistry; D015394:Molecular Structure; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013304:Streptomyces aureofaciens / Q000737:chemistry
D005609:Free Radicals; D011714:Pyrans; C013612:narasin