| Title | Asymmetric Total Synthesis of Propindilactone G, Part 2: Enantioselective Construction of the Fully Functionalized BCDE Ring System |
| Authors | Zhang, Jia-Jun You, Lin Wang, Yue-Fan Li, Yuan-He Liang, Xin-Ting Zhang, Bo Yang, Shou-Liang Su, Qi Chen, Jia-Hua Yang, Zhen |
| Affiliation | Peking Univ, State Key Lab Bioorgan Chem & Mol Engn, Minist Educ, Beijing Natl Lab Mol Sci BNLMS,Peking Tsinghua Ct, 202 Chengfu Rd, Beijing 100871, Peoples R China. Peking Univ, Dept Chem, 202 Chengfu Rd, Beijing 100871, Peoples R China. Peking Univ, Shenzhen Grad Sch, Sch Chem Biol & Biotechnol, Lab Chem Genom, Shenzhen 518055, Peoples R China. Ocean Univ China, Sch Med & Pharm, Chinese Minist Educ, Key Lab Marine Drugs, 5 Yushan Rd, Qingdao, Peoples R China. Peking Univ, State Key Lab Bioorgan Chem & Mol Engn, Minist Educ, Beijing Natl Lab Mol Sci BNLMS,Peking Tsinghua Ct, 202 Chengfu Rd, Beijing 100871, Peoples R China. Chen, JH Yang, Z (reprint author), Peking Univ, Dept Chem, 202 Chengfu Rd, Beijing 100871, Peoples R China. Yang, Z (reprint author), Peking Univ, Shenzhen Grad Sch, Sch Chem Biol & Biotechnol, Lab Chem Genom, Shenzhen 518055, Peoples R China. Yang, Z (reprint author), Ocean Univ China, Sch Med & Pharm, Chinese Minist Educ, Key Lab Marine Drugs, 5 Yushan Rd, Qingdao, Peoples R China. |
| Keywords | hydrogenolysis natural products Pauson-Khand reaction propindilactone G total synthesis PAUSON-KHAND REACTION DIASTEREOSELECTIVE TOTAL-SYNTHESIS FORMAL TOTAL-SYNTHESIS DIELS-ALDER REACTION PALLADIUM-CATALYZED HYDROGENOLYSIS CONCISE SYNTHESIS STEREOSELECTIVE-SYNTHESIS CARBONYL-COMPOUNDS AMMONIUM FORMATE CORTISTATINS |
| Issue Date | 2016 |
| Publisher | CHEMISTRY-AN ASIAN JOURNAL |
| Citation | CHEMISTRY-AN ASIAN JOURNAL.2016,11(9),1414-1424. |
| Abstract | The enantioselective synthesis of the fully functionalized BCDE tetracyclic ring system of propindilactone G (A) is reported. Several synthetic methods were developed and applied to achieve this goal, including: 1) an asymmetric Diels-Alder reaction in the presence of Hayashi's catalyst for the synthesis of optically pure key intermediate 3; 2) an intramolecular Pauson-Khand reaction (PKR) for the stereoselective synthesis of the BCDE ring with an all-carbon chiral quaternary center at the C13 position by using the TMS-substituted acetylene as the substrate; and 3) Pd-catalyzed reductive hydrogenolysis for the stereoselective synthesis of the fully functionalized BCDE tetracyclic ring system. The chemistry developed herein provided a greater understanding of the total synthesis propindilactone G (A) and its analogues. |
| URI | http://hdl.handle.net/20.500.11897/437277 |
| ISSN | 1861-4728 |
| DOI | 10.1002/asia.201600130 |
| Indexed | SCI(E) EI |
| Appears in Collections: | 化学与分子工程学院 化学生物学与生物技术学院 生物有机与分子工程教育部重点实验室 |
