河北医科大学药学院2018 Structure of Penicillin CO.H Abraham's Woodward 944.27岁 1944.58 Scheme 1.The notional reconstruction of penicillin from its degradation products. Edward Penley Abraham proposed b-lactam but opposed by Robinson Azadirachtin印楝素 The First Complete Structure Ley's Modification198 9能 CO:Me "H A品，co Correct Structure oughton.H.B.Ley.S.V.J. hem.Soc.Chem.Commun.1986.46. X-ray 1986 by Ley 天然药物化学教研室史清文教授 3河北医科大学药学院2018 天然药物化学教研室史清文教授 3 85 Structure of Penicillin • Scheme 1. The notional reconstruction of penicillin from its degradation products. • R = pent-2-enyl for the penicillin grown by fermentation in Oxford; R = benzyl for that grown in America. The difference was slightly confusing until clarified in 1943, but it did not affect the structural debates. Edward Penley Abraham proposed b-lactam but opposed by Robinson 1944, 27岁 1944, 58岁 CHO H R N O + CO2 + H2N CO2H Me HS Me H R N O S HN CO2H Me Me CO2H N H N O S Me Me CO2H R O OR R N HN S R O Me Me CO2H Abraham' s correct structure Robinson' s incorrect structure Woodward 86 The First Complete Structure MeO2C O AcO H O O H CO2Me OH O O OH O OH O Ley’s Modification 1985 MeO2C O O O O OH O AcO H O O H OH CO2Me OH Correct Structure Azadirachtin印楝素 Broughton, H. B.; Ley, S. V. J. Chem. Soc. Chem. Commun. 1986, 46. Nakanishi’s Azadirachtin 1975 X-ray 1986 by Ley