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Peking University, Sept. 22, 2011: Seven years and a half passed before the total synthesis of Schindilactone A, a natural product molecule was accomplished for the first time in the world by the research group led by Professor Yang Zhen from College of Chemistry and Molecular Engineering, Peking University. This achievement has been recently published in Angewandte Chemie , a world-renowned scientific journal that covers all aspects of chemistry. It is also the first time in recent decade that a Chinese research on total synthesis has been chosen as cover story by the magazine.
Cover Picture ( Angew. Chem. Int. Ed. 32/2011)
Schindilactone A is among a novel group of nortriterpenoids isolated by Sun Handong, CAS member and co-workers from the plants of Schisandraceae found in Yunnan Province in China. Its unique "7-8 carbocyclic system" was confirmed by using X-ray diffraction and more than 80 family compounds have been isolated so far. Study has shown that some of them possess biological activities for both favoring immune regulation and inhibiting hepatitis, tumors and HIV-1. The novelty, complexity and variety of their chemical structures are outstanding discoveries in chemistry researches on natural products, thus attracting lots of organic synthesis chemists. There have been about 10 research groups working on the synthesis of natural products in this family so far.
Strategic bond disconnections of Schindilactone A
Based on full understanding of the structure of Schindilactone A, Professor Yang's group designed an efficient and concise synthetic route consisting of 29 steps in its longest linear sequence, centered on the construction of the polycyclic ring system that allowed the first total synthesis of Schindilactone A, fully characterized and identical to those of the natural product. This synthetic strategy includes a series of salient features, which also opens a pathway for the syntheses of other related compounds, currently underway in Professor Yang’s laboratories.
Reviewers of Angewandte Chemie rated the paper as top 10 and the magazine used it for the cover picture of Issue 32, 2011. Its editor even readily offered to help with holding a press conference twice.
Extended Reading
Professor Yang studied medicinal chemistry at Shenyang college of Pharmacy and earned a PhD at Chinese University of Hong Kong in 1992 under the guidance of H. N. C. Wong. He came out postdoctoral research on natural product synthesis with K. C. Nicolaou at The Scripps Research Institute and joined its faculty in 1995. In 1998, he moved to Harvard University before returning to China as a professor at Peking University in 2001. From 2001 to 2005, he also served as a Director of Chemistry for VivoQuest Inc. and since 2005 for XTL Biopharmaceutical (both New York). His research is devoted to the total synthesis of natural products and organometallic chemistry as well as diversity-oriented synthesis and chemical biology. Up till now, he has published more than one hundred research papers on international classic magazines, such as Nature, JACS, Angew, OL, JOC and TL etc.
Angewandte Chemie is a weekly peer-reviewed scientific journal that covers all aspects of chemistry. Its impact factor was 12.730 in 2010, the highest value for a chemistry-specific journal that publishes original research. It is a journal of the German Chemical Society and is published by Wiley-VCH. Besides original research in the form of short communications, the journal contains review-type articles (reviews, minireviews, essays, highlights), and a magazine section (news, obituaries, book reviews, conference reports). Colloquially, the journal is simply called "Angewandte". "Angewandte Chemie" is German for "applied chemistry", although this translation no longer accurately describes the scope of the journal.
Written by: Chen Meng
Source: PKU News (Chinese)
Edited by: Chen Long
Reference:
Diastereoselective Total Synthesis of (±)-Schindilactone A ( Angew. Chem. Int . Ed. 32/2011)
