title: Diastereoselective total synthesis of (±)-schindilactone A, Part 2: Construction of the fully functionalized CDEFGH ring system.
abstract: The successful synthesis of the highly complex model compound (2) of the CEFGH ring system of schindilactone A (1) is described. Several synthetic methodologies were developed and applied to achieve this goal, including ring-closing metathesis (RCM) and Co-thiourea-catalyzed Pauson-Khand reactions. Furthermore, two independent approaches were developed for the construction of the GH ring of model compound 2, the key steps of which included Pd-thiourea-catalyzed carbonylative annulation, methylation, and sequential RCM/oxa-Michael-addition reactions. The chemistry developed herein has provided a greater understanding of the synthesis of schindilactone A (1) and its analogous compounds of the same family.
authors: Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, Beijing National Laboratory for Molecular Science and Peking-Tsinghua Center for Life Sciences at College of Chemistry of Peking University, Chengfu Road, 202, Beijing, 100871, China.
authors: Yong
authors: Y
authors: Li
authors: Zhi-Xing
authors: ZX
authors: Chen
authors: Qing
authors: Q
authors: Xiao
authors: Qin-Da
authors: QD
authors: Ye
authors: Tian-Wen
authors: TW
authors: Sun
authors: Fan-Ke
authors: FK
authors: Meng
authors: Wei-Wu
authors: WW
authors: Ren
authors: Lin
authors: L
authors: You
authors: Ling-Min
authors: LM
authors: Xu
authors: Yue-Fan
authors: YF
authors: Wang
authors: Jia-Hua
authors: JH
authors: Chen
authors: Zhen
authors: Z
authors: Yang
mesh_terms: D002384:Catalysis; D018360:Crystallography, X-Ray; D003500:Cyclization; D007783:Lactones / Q000737:chemistry; D008745:Methylation; D008968:Molecular Conformation; D010165:Palladium / Q000737:chemistry; D013237:Stereoisomerism; D013890:Thiourea / Q000737:chemistry; D014315:Triterpenes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D007783:Lactones; D014315:Triterpenes; C568579:schindilactone A; D010165:Palladium; D013890:Thiourea