Citation: Ming Wan, Ming Yao, Jun-Yu Gong, Peng Yang, Hua Liu, Ang Li. Synthesis of the tetracyclic core of chlorospermines[J]. Chinese Chemical Letters, ;2015, 26(3): 272-276. doi: 10.1016/j.cclet.2015.01.037 shu

Synthesis of the tetracyclic core of chlorospermines

Ming Wan ^a,b ,
Ming Yao ^b ,
Jun-Yu Gong ^b ,
Peng Yang ^b ,
Hua Liu ^a,, ,
Ang Li ^b,,

1.
a School of Pharmacy, Jiangxi University of Traditional Chinese Medicine, Nanchang 330004, China;
2.
b State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China

Corresponding author: Hua Liu, Ang Li,
Received Date: 6 January 2015
Available Online: 21 January 2015
Fund Project: Financial support was provided by Ministry of Science & Technology (No. 2013CB836900) (No. 2013CB836900)

Chlorospermines A and B are biologically interesting acridone natural products and recently isolated from Glycosmis chlorosperma. We report here a convergent approach to construct the tetracyclic core of the natural products. The two fragments are assembled together through Sonogashira coupling, and a cis-triene intermediate was prepared by using hydrosilylation/desilylation. A 6π-electrocyclization/aromatization sequence served as the key step of the synthesis, which formed the tetrasubstituted arene motif in one pot.
- Natural product synthesis,
- Electrocyclization,
- Acridone,
- Chlorospermine,
- Tetracycle
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