Journal of the American Chemical Society

Total synthesis of a C15 ginkgolide,(.+-.)-bilobalide

EJ Corey, WG Su

Index: Corey, E. J.; Su, Wei-guo Journal of the American Chemical Society, 1987 , vol. 109, # 24 p. 7534 - 7536

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Citation Number: 76

Abstract

5 X= COzCH, 8a X= H, Y= OH 6 X= CHzOH 8b X= OH, Y= H 7 X= CHO 9 X, Y= o triethylamine, as two anomers in a 4: l ratio; TLC R,-values 0.42 and 0.40, respectively, with use of 1 2 1 hexane-ethyl acetate). Reduction of 5 using lithium aluminum hydride in ether at 0" C for 1 h gave diol 6 which upon Swern oxidation in methylene chloride with 3 equiv of oxalyl chloride and 6 equiv of dimethyl sulfoxide at-45" C followed by 8 equiv of ...