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A Concise Total Synthesis of Amphidinin B

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Chinese Journal of Chemistry 2013年第1期31卷 105-110页

作者： Dongdong Wu Jinlong Wu Wei-min Dai Laboratory of Asymmetric Catalysis and Synthesis Department of Chemistry Zhejiang University Hangzhou Zhejiang 310027 China Laboratory of Advaneed Catalysis and Synthesis Department of Chemistry The Hong Kong University of Science and Technology Clear Water Bay Kowloon Hong Kong SAR China

A concise total synthesis of amphidinin B, a cytotoxic linear dicarboxylic acid associated with amphidinolide T marine macrolides, has been accomplished from the 19-membered cycloalkene intermediates designed for diverted total synthesis of amphidinolide T1 and T3-T5. The lH and 13C NMR spectra of the synthesized amphidinin B in C6D6 and CDC13 were compared with those for the natural and synthetic forms reported in the literature, showing solvent-dependence of the ^1H and ^13C NMR signals of amphidinin B in C6D6 and CDC13.

关键词： amphidinin B cycloalkene dihydroxylation oxidative cleavage total synthesis

Design and concise synthesis of gem-difluoromethylenated analogue of 7-epi-castanospermine

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Chinese Chemical Letters 2014年第8期25卷 1115-1120页

作者： Xin-Yi Jiang Xiu-Hua Xu Feng-Ling Qing Key Laboratory of Organofluorine Chemistry Shanghai Institute of Organic Chemistry Chinese Academy of Science College of Chemistry Chemical Engineering and Biotechnology Donghua University

A novel gem-difluoromethylenated castanospermine analogue B was designed and synthesized, starting from 3-bromo-3,3-difluoropropene and L-（-）-malic acid. The key steps involve substitution cyclization reaction and R... 详细信息

关键词： lndolizidine Castanospermine gem-Difluoromethylene Cyclization dihydroxylation

Asymmetric Synthesis of (3R,5R)-3-((tert-Butyldimethylsily)oxy)-5-((Z)-2-Bromovinyl)-Tetrahydro-Furan-2-one,an Intermediate for the Synthesis of Fostriecin

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Chinese Chemical Letters 2000年第11期11卷 957-960页

作者： Su Yun LIU Dao Fei HUANG Hai Hong HUANG Liang HUANG Institute of Materia Medica Chinese Academy of Medical Science&Peking Union Medical CollegeBeijing 100050

(3R,5R)-3-((tert-Butyldimethylsily)oxy)-5-((Z)-2-bromovinyl)-tetrahydro-furan-2-one, an intermediate for the synthesis of Fostriecin was achieved by intramolecular asymmetric induction in propene addition of (-)-8-phenylmenthyl glyoxylate followed by inversion of C3-hydroxyl group and Sharpless asymmetric dihydroxylation with simultaneous cyclization to give lactone 5. Then protection of C3-hydroxyl group and oxidation of the C6-primary hydroxyl group which reacted with Wittig reagent to yield the target compound 4.

关键词： Fostriecin dihydroxylation (-)-8-phenylmenthol asymmetric synthes

Study on the Synthesis of Metabolite CM2 of Clausenamide

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Chinese Chemical Letters 2003年第4期14卷 338-340页

作者： Xing Zhou LI Ke Mei WU Liang HUANG Institute of Materia Medica Chinese Academy of Medical Sciences&Peking Union Medical CollegeBeijing 100050

Synthesis of the optically active metabolite of clausenamide CM2 (3, 5-dihydroxy- 5-(a-hydroxylbenzyl)-1-methyl-4-benzylpyrrolidin-2-one) from 3-O-acetyl- clausenamide was described.

关键词： Metabolite clausenamide dehydration dihydroxylation deacylation.