Asymmetric Total Synthesis of Propindilactone G, Part 1: Initial Attempts towards the Synthesis of Schiartanes

Ling-Ming Xu; Lin You; Zhen-Hua Shan; Ruo-Cheng Yu; Bo Zhang; Yuan-He Li; Ying Shi; Jia-Hua Chen; Zhen Yang

doi:10.1002/asia.201600129

Asymmetric Total Synthesis of Propindilactone G, Part 1: Initial Attempts towards the Synthesis of Schiartanes

Chem Asian J. 2016 May 6;11(9):1406-13. doi: 10.1002/asia.201600129. Epub 2016 Apr 21.

Authors

Ling-Ming Xu¹, Lin You¹, Zhen-Hua Shan¹, Ruo-Cheng Yu¹, Bo Zhang¹, Yuan-He Li¹, Ying Shi¹, Jia-Hua Chen², Zhen Yang^{3

4

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Affiliations

¹ 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.
² 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.
³ 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.
⁴ Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Shenzhen Graduate School, Peking University, Shenzhen, 518055, P. R. China. zyang@pku.edu.cn.
⁵ 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.

PMID: 26991268
DOI: 10.1002/asia.201600129

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.

Keywords: natural products; nortriterpenoids; propindilactone G; synthetic methods; total synthesis.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Models, Molecular
Molecular Conformation
Stereoisomerism
Triterpenes / chemical synthesis*
Triterpenes / chemistry

Substances

Triterpenes
propindilactone G
schiartane