Polyether antibiotics synthesis. Total synthesis and absolute configuration of the ionophore A-23187

DA Evans, CE Sacks, WA Kleschick…

Index: Evans,D.A. et al. Journal of the American Chemical Society, 1979 , vol. 101, p. 6789 - 6791

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Citation Number: 130

Abstract

The oxime of 7-keto-7, 8, 9, 1 0-tetrahydrobenzo [a] pyrene4 was converted into its acetate, mp 193-195" C, which on heating with Pd/C in naphthalene at 200-205" C for 2 h yielded after dry column chromatographyi5 36% 1, mp 203-204" C; NMR showed two exchangeable protons at 6 4.66. Anal. I (C2oH l3N) C, H, N. To a stirred mixture under Nz of 2.18 g of NaBF4 in 50 mL of dry THF was added 2.6 mL of CF3COOH followed by 1.07 g of 1. After ...