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Total synthesis of (+)-negamycin and its 5-epi-derivative |
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| Authors: | Shigenobu Nishiguchi Akihiro Taguchi Tetsuya Kajimoto Yuri Yamazaki Yoshiaki Kiso |
| Institution: | a Department of Medicinal Chemistry, Kyoto Pharmaceutical University, Kyoto 607-8412, Japan b Pharmaceutical Manufacturing Chemistry, Kyoto Pharmaceutical University, Kyoto 607-8412, Japan c Department of Medicinal Chemistry, School of Pharmacy, Tokyo University of Pharmacy and Life Sciences, Tokyo 192-0392, Japan |
| Abstract: | (+)-Negamycin was prepared in 13 steps in an overall yield of 31% from commercially available ethyl (R)-(+)-4-chloro-3-hydroxybutanoate. The key step in the reaction sequence was a highly stereoselective asymmetric Michael addition of chiral amine (−)-21 (1S,2R)-(−)-2-methoxybornyl-10-benzylamine] into the α,β-unsaturated carbonyl moiety of key intermediate 8, thus establishing the second chiral center in (+)-negamycin. 5-epi-Negamycin was also prepared in a similar fashion. |
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