News&Event
Congratulations to Prof. Yang on winning the first class prize of the Shenzhen Natural Science Award for 2013.
The Shenzhen government announced the Shenzhen Scientific and Technical Awards for 2013 on 2014 Dec 18th. Professor Yang, with his research in “the total synthesis of natural products with significant biological activities” won the first class prize of the Shenzhen Natural Science Award. And this’s the only one in the first class, the other four projects won the second class prize.
Prof. Yang received the certificate of award on the ceremony
Before the ceremony, Prof. Yang was interviewed by the Shenzhen TV.
The selected achievements of the group in the project of “the total synthesis of natural products with significant biological activities”
90.Total Synthesis of Maoecrystal V
Wei-Bin Zhang, Dr. Guang Lin, Wen-Bin Shao, Dr. Jian-Xian Gong,* and Prof. Dr. Zhen Yang*
Maoecrystal V (1) is a novel diterpenoid, which was originally isolated from the leaves of the Chinese medicinal herb Isodon eriocalyx in 2004 by Sun et al.1 It has been found to be selectively cytotoxic towards HeLa cells, with an IC50 value of 20 ng mL−1. Significant research efforts have been devoted to the synthesis of maoecrystal V because of its intriguing biological properties, rarity in nature, and complex structural features. Herein, we describe our recent investigations, which have culminated in the total synthesis of (±)-maoecrystal V. The current strategy involved three key steps for the successful construction of the key tetrahydrofuran oxa-bridge skeleton, including a Wessely oxidative dearomatization, a novel intramolecular Diels–Alder reaction, and a RhII-catalyzed O[BOND]H insertion reaction.
89. Asymmetric Total Synthesis of (−)-Cebulactam A1
Shouliang Yang, Yumeng Xi, Jia-Hua Chen* and Zhen Yang*
Org. Chem. Front., 2014, 1, 91-99
The total synthesis of (−)-cebulactam A1 (3) has been achieved for the first time in 18 steps. The key steps in this synthesis included an asymmetric chelation-controlled vinylogous Mukaiyama aldol reaction for the stereoselective synthesis of the stereogenic centers at the C8 and C9 positions, an intramolecular SmI2-mediated Reformatsky reaction for the formation of a macrocyclic lactam, and an SN2′ reaction for the stereoselective formation of the (E)-double bond linked tetrahydropyran moiety of cebulactam A1 (3).
88.Asymmetric total synthesis of (−)-lingzhiol via a Rh-catalysed [3+2] cycloaddition
Rong Long, Jun Huang, Wenbin Shao, Song Liu, Yu Lan*, Jianxian Gong*, Zhen Yang*
The development of efficient reactions for the one-pot construction of bicyclic ring systems bearing two quaternary carbon centres at their bridgehead positions represents a significant challenge to synthetic chemistry. The development of new methods capable of overcoming this challenge is highly desirable, because this motif can be found in a wide range of natural products with significant biological activities. Herein, we report an efficient [3+2] cycloaddition reaction between an enal and an alleno rhodium species, which was generated in situ from the corresponding enynol via a retro metal-propargylation reaction, to give [3.3.0] and [3.4.0] bicyclic systems bearing two quaternary atoms at their bridgehead positions. The developed chemistry has been successfully applied to the asymmetric total synthesis of natural product (−)-lingzhiol (4) for the first time in 17 steps.
87.Total synthesis of (+)-fusarisetin A
Jun Huang, Lichao Fang, Jianxian Gong, Chuangchuang Li, Zhen Yang*
Herein we report the full details of our efforts toward the application of Pauson–Khand reaction for the stereoselective construction of the trans-decalin subunit with a C16 quaternary stereocenter of fusarisetin A, which led to the asymmetric total synthesis of (+)-fusarisetin A. The developed chemistry provides an alternative strategy to the intramolecular Diels–Alder reaction that has been employed for the synthesis of trans-decalin based natural products.
