Enantioselective synthesis of N1999A2

…, H O'Dowd, BM Rosen, AG Myers

Index: Ji, Nan; O'Dowd, Hardwin; Rosen, Brad M.; Myers, Andrew G. Journal of the American Chemical Society, 2006 , vol. 128, # 46 p. 14825 - 14827

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Citation Number: 25

Abstract

An enantioselective synthetic route to the enediyne antibiotic N1999A2 (1) is described, proceeding in 21 steps (0.4% yield, 77% average yield per step) from (R)-(+)-glycidol. The route involves the convergent assembly of three components: a (1-iodovinyl) stannane (2), a 1, 5-hexadiyne-3, 4-diol derivative (3), and a substituted naphthoic acid (4). Important transformations in the synthetic sequence include the palladium-catalyzed coupling of 2 ...