What can organic chemist Do with np? What Can Organic Chemist Do With NP? First Bio-mimic Synthesis C-E-a 6195 netic total synthesis of tropinone (Robinson.1917 Mimic Synthesis inspiration for Nature Examples of Structure Elucidation 65 高 天然产物化学促进生命科学的发展 Natural products as chemical probes 漫有天然产物就没有分子生物学的今天：4 Biomimetic total synthesis of tropinone (Robinson, 1917) (1) Robinson, R. J. Chem. Soc., Trans. 1917, 762. (2) Robinson, R. J. Chem. Soc., Trans. 1917, 762. (3) See also: Birch,A. J. Notes Records Royal Soc. London 1993, 47, 277. First Bio-mimic Synthesis mimic Synthesis 1886-1975 1947年Nobel Prize R. Robinson CHO CHO + H2NMe + COOH COOH O Aqua N O Me What Can Organic Chemist Do With NP? What Can Organic Chemist Do With NP? What Can Organic Chemist Do With NP? What Can Organic Chemist Do With NP? 英国Nottingham 大学的Gerald Pattenden发明了用一步反应合成甾体化 合物四个环和7个手性中心的简易巧妙方法。 Gerald Pattenden Nature, 2008, 445, 323-332. Natural products as inspiration for the development of asymmetric catalysis SePh CH3 CH3 CH3 H CH3 H O O n-Bu2SnH, AlBN Heat Redical cascade H CHO OHC HN i) CH3NH2 ii) AcOH 65% C.H. Heathcock see PNAS 1996, 63, 14323 Methyl Homosecodaphniphyllate Daphniphyllum macropodum 虎皮楠 C.H. Heathcock Science, 1990, 248, 1532-1534. Mimic Synthesis Mimic Synthesis inspiration for Nature Examples of Structure Elucidation O HO NCH3 H HO H N O H H H H O H N Morphine 118 Years! Strychnine 127 Years! Robert Robinson published 54 paper for structure elucidation And determined it in 1946 and got Nobel Prize in 1947. Robert B. Woodward Total Syn. In 1954. Robert Robinson 1925 (1886-1975) 1952 Total Syn By Gates 高怡生 曾广方 天然产物作为化学和生物学之间一个天然的通道，是大自然经过漫 长的筛选和进化选择出来的。生命科学的发展急需应用新的小分子作为 分子探针去帮助研究已知的生物反应机理，去发现尚未被阐明的生物作 用机理，去验证全新的生物药物靶点，和去解决重大的医学难题。天然 产物作为化学小分子探针做出了其他生物技术方法无法企及的特殊贡 献，并此催生了一门新的学科——(天然产物)化学生物学。 天然产物化学促进生命科学的发展 Erin E. Carlson. Natural Products as Chemical Probes. ACS Chem. Biol. 2010, 5, 639-653. Stuart L. Schreiber, Harvard Uni. Natural Products as Chemical Probes Natural Products as Chemical Probes 没有天然产物就没有分子生物学的今天?