Conformationally selective transannular cyclizations of humulene 9,10-epoxide. Synthesis of the two skeletally different cyclohumulanoids: dl-bicyclohumulenone and dl-africanol |
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Authors: | Haruhisa Shirahama Kiyoharu Hayano Yoshiro Kanemoto Shunjiro Misumi Toshikazu Ohtsuka Nobuhiro Hashiba Akio Furusaki Shizuaki Murata Ryoji Noyori Takeshi Matsumoto |
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Institution: | 1. Department of Chemistry, Faculty of Science, Nagoya University, Chikusa-ku, Nagoya 464, JAPAN |
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Abstract: | Two cyclohumulanoids, dl-bicyclohumulenone () and dl-africanol ( were synthesized through newly developed conformationally selective transannular cyclization of humulene 9,10-epoxide (). The epoxide was converted to a bicyclohumulenediol diacetate in 70% yield by treatment with BF3·OEt2-Ac2O, while treatment of with trimethylsilyl trifluoromethansulfonate gave an africen-10-ol (a and b) in 80% yield. The two intermediates and furnished the natural products and in 30 and 8 % yield from respectively. |
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