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Total synthesis and structure revision of deacetylravidomycin M |
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| Authors: | Akimi BenDay-Shin Hsu Takashi Matsumoto Keisuke Suzuki |
| Institution: | Department of Chemistry, Tokyo Institute of Technology, 2-12-1 O-okayama, Meguro-ku, Tokyo 152-8551, Japan |
| Abstract: | Total synthesis of the unnatural enantiomer of deacetylravidomycin M was accomplished. The key steps include, (1) aryl C-glycosidation of the azido-bearing fucosyl acetate 2 by using catalytic Sc(OTf)3, (2) the 2+2] cycloaddition reaction of alkoxybenzyne bearing an azido sugar to ketene silyl acetal, and (3) the ring expansion reaction of alkoxybenzocyclobutenone. The synthesis revealed that the natural product is not the proposed amine, but the corresponding N-oxide. |
| Keywords: | Ravidomycin Aryl C-glycoside O&rarr C-Glycoside rearrangement [2+2] Cycloaddition Ring expansion reaction Total synthesis |
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