title: Asymmetric Total Synthesis of Propindilactone G, Part 1: Initial Attempts towards the Synthesis of Schiartanes.
abstract: Our first-generation synthetic study towards the total synthesis of propindilactone G (1) and its analogues is reported. The key synthetic steps were an intramolecular Pauson-Khand reaction (PKR) and a vinylogous Mukaiyama reaction (VMAR). The stereoselective synthesis of the CDE ring moiety with an all-carbon quaternary center through a PKR was difficult, whilst a VMAR afforded a product with the opposite stereochemistry at the C20 position on the side chain. These results led us to redesign our synthetic strategy for the total synthesis of compound 1.
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: Ling-Ming
authors.initials: LM
authors.lastname: Xu
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: Zhen-Hua
authors.initials: ZH
authors.lastname: Shan
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: Ruo-Cheng
authors.initials: RC
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.
authors.forename: Bo
authors.initials: B
authors.lastname: Zhang
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: Ying
authors.initials: Y
authors.lastname: Shi
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: D008958:Models, Molecular; D008968:Molecular Conformation; D013237:Stereoisomerism; D014315:Triterpenes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D014315:Triterpenes; C000621059:propindilactone G; C512130:schiartane
keywords: natural products; nortriterpenoids; propindilactone G; synthetic methods; total synthesis