News&Event
Mr. Zhang Pengpeng Wins Second Prize of 2017 ACS Shanghai Chapter Outstanding Graduate Student Research Award
Prof. Yang and Prof. Gong titled as Excellent Research Advisors.
Wenbin Shao and Yuanyuan Chang have successfully defended their dissertations
Wenbin Shao and Yuanyuan Chang have successfully defended their dissertations and shall be conferred the doctor’s degree. Congratulations!
Congratulation to Mr. Zhang for his work was published on JACS!
For more details, please see the paper online:
https://web.pkusz.edu.cn/yang/121/
or
121. Enantioselective Total Synthesis of (−)-Pavidolide B
Peng-Peng Zhang, Zhi-Ming Yan, Yuan-He Li, Jian-Xian Gong*, and Zhen Yang*
J. Am. Chem. Soc., 2017, 139 , 13989–13992
• Second Most Read Articles in JACS 2017/10.
• Highlighted in Synfacts, 2017, 13, 1233.
• Highlighted in Org. Chem. Highlights 2017, April 2.
• Highlighted in ChemistryWorld, 2017, Nov, 1.
• Highlighted in Chin. J. Org. Chem. 2018, 38, 282.
The enantioselective synthesis of (−)-pavidolide B (1) was achieved in a linear sequence of 10 steps. The key steps are (a) an enantioselective organocatalytic cyclopropanation; (b) a radical-based cascade annulation for the regio- and diastereo-selective synthesis of the highly functionalized lactone 3 bearing the characteristic tricyclic core and seven contiguous stereocenters; (c) a sequential ring-closing metathesis reaction and a RhCl3-catalyzed double bond isomerization to form the seven-membered D ring of (−)-pavidolide B.
120.Total synthesis of orientalol F via gold-catalyzed cycloisomerization of alkynediol
Org. Chem. Front., 2017, 4, 2296-2300
The total synthesis of orientalol F has been achieved starting from 1,4-dioxaspirodecan-8-one 11 in 13 steps. The key steps in this synthesis feature: (1) gold-catalyzed tandem cycloisomerization of alkynediol 10 for the formation of its seven-membered oxa-bridged bicyclic skeleton 9 of orientalol F, (2) visible-light-promoted organocatalytic aerobic oxidation of silyl enol ether 16 to enone 17, (3) Barbier-type butenylation for the diastereoselective synthesis of allylic alcohol 18 from enone 17, and (4) substrate-controlled Pd-catalyzed hydrogenation of 20 for the stereoselective installation of the C1 stereogenic center of 8.
