title: Asymmetric Total Synthesis of Propindilactone G, Part 3: The Final Phase and Completion of the Synthesis.
abstract: Two independent synthetic approaches were evaluated for the final phase of the asymmetric total synthesis of propindilactone G (1). The key steps that led to the completion of the asymmetric total synthesis included: 1) an intermolecular oxidative heterocoupling reaction of enolsilanes to link the core structure to the side chain; 2) an intermolecular Wittig reaction for the formation of the α,β,γ,δ-unsaturated ester; and 3) a regio- and stereoselective OsO4 -catalyzed dihydroxylation of an α,β,γ,δ-unsaturated enone, followed by an intramolecular lactonization reaction to afford the final product. These reactions enabled the synthesis of (+)-propindilactone G in only 20 steps. As a consequence of our synthetic studies, the structure of (+)-propindilactone G has been revised. Furthermore, the direct oxidative coupling strategy for ligation of the core of propindilactone G with its side chain may find application in the syntheses of other natural products and complex molecules.
authors.affiliation: State Key Laboratory of Bioorganic Chemistry and Molecular Engineering of the Ministry of Education, Beijing National Laboratory for Molecular Science (BNLMS), Peking-Tsinghua Center for Life Sciences, and, Department of Chemistry, Peking University, 202 Chengfu Road, Beijing, 100871, P. R. China.
authors.forename: Xin-Ting
authors.initials: XT
authors.lastname: Liang
authors.affiliation: State Key Laboratory of Bioorganic Chemistry and Molecular Engineering of the Ministry of Education, Beijing National Laboratory for Molecular Science (BNLMS), Peking-Tsinghua Center for Life Sciences, and, Department of Chemistry, Peking University, 202 Chengfu Road, Beijing, 100871, P. R. China.
authors.forename: Lin
authors.initials: L
authors.lastname: You
authors.affiliation: State Key Laboratory of Bioorganic Chemistry and Molecular Engineering of the Ministry of Education, Beijing National Laboratory for Molecular Science (BNLMS), Peking-Tsinghua Center for Life Sciences, and, Department of Chemistry, Peking University, 202 Chengfu Road, Beijing, 100871, P. R. China.
authors.forename: Yuan-He
authors.initials: YH
authors.lastname: Li
authors.affiliation: State Key Laboratory of Bioorganic Chemistry and Molecular Engineering of the Ministry of Education, Beijing National Laboratory for Molecular Science (BNLMS), Peking-Tsinghua Center for Life Sciences, and, Department of Chemistry, Peking University, 202 Chengfu Road, Beijing, 100871, P. R. China.
authors.forename: Hai-Xin
authors.initials: HX
authors.lastname: Yu
authors.affiliation: State Key Laboratory of Bioorganic Chemistry and Molecular Engineering of the Ministry of Education, Beijing National Laboratory for Molecular Science (BNLMS), Peking-Tsinghua Center for Life Sciences, and, Department of Chemistry, Peking University, 202 Chengfu Road, Beijing, 100871, P. R. China. jhchen@pku.edu.cn.
authors.forename: Jia-Hua
authors.initials: JH
authors.lastname: Chen
authors.affiliation: State Key Laboratory of Bioorganic Chemistry and Molecular Engineering of the Ministry of Education, Beijing National Laboratory for Molecular Science (BNLMS), Peking-Tsinghua Center for Life Sciences, and, Department of Chemistry, Peking University, 202 Chengfu Road, Beijing, 100871, P. R. China. zyang@pku.edu.cn.|Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Shenzhen Graduate School, Peking University, Shenzhen, 518055, P. R. China. zyang@pku.edu.cn.|Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, 5 Yushan Road, Qingdao, P. R. China. zyang@pku.edu.cn.
authors.forename: Zhen
authors.initials: Z
authors.lastname: Yang
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis / Q000737:chemistry; D004952:Esters / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism; D014315:Triterpenes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D001688:Biological Products; D004952:Esters; D007659:Ketones; D014315:Triterpenes; C000621059:propindilactone G
keywords: cross-coupling; dihydroxylation; enolsilanes; propindilactone G; total synthesis