Advances in the Total Synthesis of Xanthanolide-Type Sesquiterpenoids

Xiaoqiang Lei; Juan Feng; Jingchun Liu; Yefeng Tang

doi:10.1002/asia.201900040

Advances in the Total Synthesis of Xanthanolide-Type Sesquiterpenoids

Chem Asian J. 2019 Jun 3;14(11):1888-1899. doi: 10.1002/asia.201900040. Epub 2019 Apr 16.

Authors

Xiaoqiang Lei¹, Juan Feng^{1

2}, Jingchun Liu¹, Yefeng Tang^{1

3}

Affiliations

¹ School of Pharmaceutical Sciences, MOE Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology, Tsinghua University, Beijing, 100084, China.
² School of Pharmaceutical Sciences, Beijing Area Major Laboratory of Peptide & Small Molecular Drugs, Engineering Research Center of Endogenous Prophylactic of Ministry of Education of China, Beijing Laboratory of Biomedical Materials, Capital Medical University, Beijing, 100069, China.
³ Collaborative Innovation Center for Biotherapy, State Key Laboratory of Biotherapy and Cancer Center, West China Medical School, Sichuan University, Chengdu, 610041, China.

PMID: 30835959
DOI: 10.1002/asia.201900040

Abstract

Xanthanolide-type sesquiterpenoids are a diverse family of natural products isolated primarily from the genus Xanthium (Compositae). The intriguing molecular architectures and biological profiles of these natural products have rendered them attractive targets for total synthesis. This focus review aims to provide an up-to-date summary of progress in the chemical synthesis of xanthanolide-type sesquiterpenoids. Different synthetic strategies to form 5/7-cis- and 5/7-trans-bicyclic xanthanolides are presented in chronological order, with an emphasis on the key elements used to forge the characteristic 5/7-bicyclic cores of the targets. Recent advances in the total syntheses of structurally more complicated polycyclic and dimeric xanthanolides are also discussed.

Keywords: natural products; pungiolides; sesquiterpene lactones; total synthesis; xanthanolides.

Publication types

Review

Abstract

Publication types

Grants and funding