Nature Is A Great Architecture Why so much chemical diversity is generated by organisms? HO OH CH3 HO HO AcO HO HO -CH H AcO HO HOAcOCinn HO H OH 00 Ryanodine Ginkgolide C 0 CO2Me 00 OCH3 Echinopine B Aco Meo2C OH Maoecrystal Z CH3 H Azadiractin Morphine OH 、H NH2 OH OHH NH H3C N Huperzine A HO OH HO H CH3 Ajmaline Tetrodotoxin Strychnine OH CH OH OH CO2CH3 OH H20 Vinigrol Metaphanine Gelsemine Khayasin
Science,2020,367:676-681. A Classic taxane core B Complex taxane core K.C.Nicolaou et al J.Am.Chem.Soc.2010, 132:3815-3818. OH Taxol (1) OH ARTICLES Published on Wab 2/2010 OH Total Synthesis of Echinopines A and B K.Ding,an-Alexandro Pchard and David YK Chon Structural features AcO ereo neopentyl positons( Abstract Echinopine A and B)-and)two naturally ooouring compounds characterized with zed in bo位 oN) Fig-1.Comparison of the ne (2) 、6 ve22 ovich 2骨城B COR Results and Discussion R 55 5 Fig.2.analysis of(-)-canataxpropelane(2)
ORGANIC LETTERS Echinopines A and B:Sesquiterpenoi 2008 2010,/32X11:3815.3818. Possessing an Unprecedented Skeletovo10.No.5 Total Synthesis of Echinopines A and B from Echinops spinosus 701-704 K.C.Nicdlaou,"Hanfeng Ding,Jean-Alexandre Richard,and David Y.K.Chen" Mei Dong,t Bin Cong Shu-Hong Yu,t Francoise Sauriol,Chang-Hong Huo, Novombor ,200 E-mal::david_chenicsa-stardu.g Qing-Wen Shi,"t Yu-Cheng Gu,S Lolita O.Zamir,and Hiromasa Kiyota" Hebei Medical University,361 Zhongshan East Road, Tetoalynthesmowesaneertanmosolbrhohmeatayzedoyekpopanatona-1oanda 050017,Shijiazhuang,Hebei Province,People's Republic of China samarium dodde-mediated ring closure (3-37). shiqingwen@hebmu.edu.ns ABSTRACT 次 co 王R:ea A Synthesis of Echinopine B** Theo D.Michels,Matthew S.Dowling,and Christopher D.Vanderwa R=H R=CHa Angew Chem Int Ed Engl 2012,51(30):7572-7576.I Echinopines A and B(I and 2)are sesquiterpenes isolated Formal asymmetric synthesis of Echinopine A and B by Kiyota and co-workers from the root of the plant Echinops Chen et al,Angew.Chem.Int.Ed,2011,50,1-5 spinosus and they probably originate from biosynthetic modification of the guaiane framework(see 3).In spite of the H -COR R=H->Echinopine A R=Me-Echinopine B 1112 1:R=H:echinopine A 3:cis-guaiane 2:R=Me:echinopine B skeleton
初级代谢产物&二级代谢产物一天然产物 次级代谢 歧霉素 初级代谢 OH 类异成二烯 有效害素入 R 0 S-CaA H MP. 9o1 NR 万古寄 H.N 碱 杆 表柔比星 金做害
Molecular Building Blocks of Life OH HO OH OH amino acids fatty acids carbohydrates nucleobases mono- glycerol nucleotides saccharides proteins phospholipids poly- DNA/RNA saccharides 88898 AVAMAAY Primary Metabolites-Biochemistry