| Biomimetically inspired total synthesis of (12S)-12-hydroxymonocerin and (12R)-12-hydroxymonocerin | |
| Department | OSSO国家重点实验室 |
| Fang BW(方博文)1; Xie XG(谢新刚)1; Jing P(靖鹏)1; Zhao CG(赵常贵)1; Li HL(李辉林)1; Ma, Haichen1; She XG(厍学功)1,2; She XG(厍学功) | |
| 2013 | |
| Source Publication | Tetrahedron
 |
| ISSN | 0040-4020 |
| Volume | 69Issue:51Pages:11025-11030 |
| Abstract | A concise asymmetric total synthesis of (12S)-12-hydroxymonocerin (1) and (12R)-12-hydroxymonocerin (2) were efficiently achieved from the known 4-bromo-2,6-dimethoxyphenol. The synthetic approach was inspired by our biomimetic synthesis of (+)-monocerin (3) and 7-O-demethylmonocerin (4). The cis-fused furobenzopyranones of 1 and 2 was efficiently constructed via an intramolecular nucleophilic trapping of a quinonemethide intermediate, which was obtained by benzylic oxidation of compound 10 using 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ). |
| Keyword | Biomimetically Inspired Total Synthesis Cis-fused Furobenzopyranone (12s)-12-hydroxymonocerin (12r)-12-hydroxymonocerin Anion Relay Chemistry |
| Subject Area | 物理化学与绿色催化 |
| DOI | 10.1016/j.tet.2013.09.075 |
| Funding Organization | the NSFC (21125207;21102062;21072086);the MOST (2010CB833203);PCSIRT (IRT1138);the FRFCU (lzujbky-2013-49;lzujbky-2013-ct02);Program 111 |
| Indexed By | SCI |
| If | 2.817 |
| Language | 英语 |
| compositor | 第二作者单位 |
| Citation statistics | |
| Document Type | 期刊论文 |
| Identifier | http://ir.licp.cn/handle/362003/4979 |
| Collection | 羰基合成与选择氧化国家重点实验室（OSSO） |
| Corresponding Author | She XG(厍学功) |
| Affiliation | 1.Lanzhou Univ, Dept Chem, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China 2.Chinese Acad Sci, Lanzhou Inst Chem Phys, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China |
| Recommended Citation GB/T 7714 | Fang BW,Xie XG,Jing P,et al. Biomimetically inspired total synthesis of (12S)-12-hydroxymonocerin and (12R)-12-hydroxymonocerin[J]. Tetrahedron,2013,69(51):11025-11030. |
| APA | Fang BW.,Xie XG.,Jing P.,Zhao CG.,Li HL.,...&厍学功.(2013).Biomimetically inspired total synthesis of (12S)-12-hydroxymonocerin and (12R)-12-hydroxymonocerin.Tetrahedron,69(51),11025-11030. |
| MLA | Fang BW,et al."Biomimetically inspired total synthesis of (12S)-12-hydroxymonocerin and (12R)-12-hydroxymonocerin".Tetrahedron 69.51(2013):11025-11030. |
| Files in This Item: | ||||||
| File Name/Size | DocType | Version | Access | License | ||
| Tetrahedron, 2013, 6（410KB） | 期刊论文 | 作者接受稿 | 开放获取 | CC BY-NC-SA | View Application Full Text | |
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