Issue 20, 2014
From the journal:

Organic & Biomolecular Chemistry

Total synthesis of lycorine-type alkaloids by cyclopropyl ring-opening rearrangement†

Dandan Liu,ab   Long Ai,a   Fan Li,b   Annan Zhao,a   Jingbo Chen,a   Hongbin Zhanga  and  Jianping Liu*a  

* Corresponding authors

a Key Laboratory of Medicinal Chemistry for Natural Resource (Yunnan University), Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming, Yunnan 650091, P. R. China
E-mail: jpliu@ynu.edu.cn
Fax: +86-871-65035538

b School of Pharmaceutical Sciences and Yunnan Key Laboratory of Pharmacology for Natural Products, Kunming Medical University, 1168 Western Chunrong Road, Yuhua Street, Chenggong New City, Kunming, Yunnan 650500, P. R. China

Abstract

A practical method for the synthesis of lycorine-type alkaloids with cis-B/C ring structure has been developed. Based on the reactions of aminocyclization, palladium-mediated arylation and especially cyclopropyl ring-opening rearrangement, the synthesis of anhydrocaranine, (±)-γ-lycorane and putative (±)-amarbellisine was accomplished.

Graphical abstract: Total synthesis of lycorine-type alkaloids by cyclopropyl ring-opening rearrangement

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Article information

DOI
https://doi.org/10.1039/C4OB00126E
Article type
Paper
Submitted
17 Jan 2014
Accepted
11 Mar 2014
First published
11 Mar 2014

Org. Biomol. Chem., 2014,12, 3191-3200

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Total synthesis of lycorine-type alkaloids by cyclopropyl ring-opening rearrangement

D. Liu, L. Ai, F. Li, A. Zhao, J. Chen, H. Zhang and J. Liu, Org. Biomol. Chem., 2014, 12, 3191 DOI: 10.1039/C4OB00126E

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