title: Diastereoselective total synthesis of (±)-schindilactone A, Part 1: Construction of the ABC and FGH ring systems and initial attempts to construct the CDEF ring system.
abstract: First-generation synthetic strategies for the diastereoselective total synthesis of schindilactone A (1) are presented and methods for the synthesis of the ABC, FGH, and CDEF moieties are explored. We have established a method for the synthesis of the ABC moiety, which included both a Diels-Alder reaction and a ring-closing metathesis as the key steps. We have also developed a method for the synthesis of the FGH moiety, which involved the use of a Pauson-Khand reaction and a carbonylative annulation reaction as the key steps. Furthermore, we have achieved the construction of the central 7-8 bicyclic ring system by using a [3,3]-rearrangement as the key step. However, unfortunately, when this rearrangement reaction was applied to the construction of the more advanced CDEF moiety, the anticipated annulation reaction did not occur and the development of an alternative synthetic strategy would be required for the construction of this central core.
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, College of Chemistry of Peking University, 202 Chengfu Road, Beijing 100871, China.
authors: Tian-Wen
authors: TW
authors: Sun
authors: Wei-Wu
authors: WW
authors: Ren
authors: Qing
authors: Q
authors: Xiao
authors: Ye-Feng
authors: YF
authors: Tang
authors: Yan-Dong
authors: YD
authors: Zhang
authors: Yong
authors: Y
authors: Li
authors: Fan-Ke
authors: FK
authors: Meng
authors: Yi-Fan
authors: YF
authors: Liu
authors: Ming-Zhe
authors: MZ
authors: Zhao
authors: Ling-Min
authors: LM
authors: Xu
authors: Jia-Hua
authors: JH
authors: Chen
authors: Zhen
authors: Z
authors: Yang
mesh_terms: D018360:Crystallography, X-Ray; D061565:Cycloaddition Reaction; D008968:Molecular Conformation; D013237:Stereoisomerism; D014315:Triterpenes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D014315:Triterpenes; C568579:schindilactone A