Combinational O-aryl carbamate and benzamide directed ortho metalation reactions. Synthesis of ochratoxin A and ochratoxin B

MP Sibi, S Chattopadhyay, JW Dankwardt…

Index: Sibi,M.P.; Chattopadhyay,S.; Dankwardt,J. Journal of the American Chemical Society, 1985 , vol. 107, p. 6312

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Citation Number: 44

Abstract

Abstract: The syntheses of isocoumarins 9a and 9b, known penultimate precursors for the toxic fungal metabolites ochratoxin B (3a) and ochratoxin A (3b), respectively, are reported. The syntheses are initiated from 0-aryl carbamates 4a, b and proceed through intermediates 5c, d, 7c, d, and 8b, c by a synthetic design that involves comprehensive application of the directed ortho metalation reaction on 0-aryl carbamates and tertiary benzamides.