Diastereoselective Total Synthesis of (+/-)-Schindilactone A, Part 3: The Final Phase and Completion
文献类型：期刊论文
| 作者 | Ren, Wei-Wu1,2,3; Chen, Zhi-Xing1,2,3; Xiao, Qing1,2,3; Li, Yong1,2,3; Sun, Tian-Wen1,2,3; Zhang, Zi-Yang1,2,3; Ye, Qin-Da1,2,3; Meng, Fan-Ke1,2,3; You, Lin1,2,3; Zhao, Ming-Zhe1,2,3 |
| 刊名 | CHEMISTRY-AN ASIAN JOURNAL
 |
| 出版日期 | 2012-10-01 |
| 卷号 | 7期号:10页码:2341-2350 |
| 关键词 | Fused-ring Systems Natural Products Schindilactone a Synthetic Methods Total Synthesis |
| ISSN号 | 1861-4728 |
| DOI | 10.1002/asia.201200365 |
| 英文摘要 | The final phase for the total synthesis of (+/-)-schindilactone A (1) is described herein. Two independent synthetic approaches were developed that featured Pdthiourea-catalyzed cascade carbonylative annulation reactions to construct intermediate 3 and a RCM reaction to make intermediate 4. Other important steps that enabled the completion of the synthesis included: 1) A Ag-mediated ring-expansion reaction to form vinyl bromide 17 from dibromocyclopropane 30; 2) a Pd-catalyzed coupling reaction of vinyl bromide 17 with a copper enolate to synthesize ketoester 16; 3) a RCM reaction to generate oxabicyclononenol 10 from diene 11; 4) a cyclopentenone fragment in substrate 8 was constructed through a Cothiourea-catalyzed PausonKhand reaction (PKR); 5) a Dieckmann-type condensation to successfully form the A ring of schindilactone A (1). The chemistry developed for the total synthesis of schindilactone A (1) will shed light on the synthesis of other family members of schindilactone A. |
| 语种 | 英语 |
| WOS记录号 | WOS:000308877400024 |
| 出版者 | WILEY-V C H VERLAG GMBH |
| 源URL | [http://ir.iccas.ac.cn/handle/121111/47569]  |
| 专题 | 中国科学院化学研究所 |
| 通讯作者 | Tang, Ye-Feng |
| 作者单位 | 1.Peking Univ, Shenzhen Grad Sch, Sch Chem Biol & Biotechnol, Lab Chem Genom, Shenzhen 518055, Peoples R China 2.Peking Univ, Key Lab Bioorgan Chem & Mol Engn, Minist Educ, BNLMS, Beijing 100871, Peoples R China 3.Peking Univ, Coll Chem, Peking Tsinghua Ctr Life Sci, Beijing 100871, Peoples R China |
| 推荐引用方式 GB/T 7714 | Ren, Wei-Wu,Chen, Zhi-Xing,Xiao, Qing,et al. Diastereoselective Total Synthesis of (+/-)-Schindilactone A, Part 3: The Final Phase and Completion[J]. CHEMISTRY-AN ASIAN JOURNAL,2012,7(10):2341-2350. |
| APA | Ren, Wei-Wu.,Chen, Zhi-Xing.,Xiao, Qing.,Li, Yong.,Sun, Tian-Wen.,...&Yang, Zhen.(2012).Diastereoselective Total Synthesis of (+/-)-Schindilactone A, Part 3: The Final Phase and Completion.CHEMISTRY-AN ASIAN JOURNAL,7(10),2341-2350. |
| MLA | Ren, Wei-Wu,et al."Diastereoselective Total Synthesis of (+/-)-Schindilactone A, Part 3: The Final Phase and Completion".CHEMISTRY-AN ASIAN JOURNAL 7.10(2012):2341-2350. |
入库方式： OAI收割
来源：化学研究所
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