Synthesis of the anti-virus compound shuangkangsu's analogs.
Four novel cyclic peroxide glucosides 15a, 15b, 16a, and 16b, optically pure analogs of shuangkangsu (1), which is an anti-virus natural product with an unusual skeleton isolated from the buds of Lonicera japonica Thunb, were first synthesized totally in six steps including cycloaddition of furan with diethyl acetylenedicarboxylate and glycosylation.
Li
Di-Zao
DZ
The Key Laboratory of Bioactive Substances and Resources Utilization of Chinese Herbal Medicine, Peking Union Medical College, Ministry of Education, Beijing, China.
Tang
Yan-Bo
YB
Kang
Zhi-Yun
ZY
Chen
Ruo-Yun
RY
Yu
De-Quan
DQ
D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D004146:Dioxanes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D006031:Glycosylation; D031239:Lonicera / Q000737:chemistry*; D015394:Molecular Structure; D009005:Monosaccharides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D019906:Nuclear Magnetic Resonance, Biomolecular; D009975:Orthomyxoviridae / Q000187:drug effects; D010084:Oxidation-Reduction; D012136:Respiratory Syncytial Viruses / Q000187:drug effects
C539038:5,8-divinyl-1,4-dihydro-1,4-di-O-beta-D-glucopyranosyl-2,3-dioxane; D000998:Antiviral Agents; D004146:Dioxanes; D009005:Monosaccharides