Issue 11, 2021
From the journal:

Organic Chemistry Frontiers

Construction of the tetracyclic core of the Lycopodium alkaloid annotinolide C†

Xiang Guo,a   Yong-Yao Li,a   Shuang-Hu Wang,a   Fu-Min Zhang, ORCID logo *a   Bao-Sheng Li, ORCID logo *b   Yong-Qiang Tu ORCID logo *ac  and  Xiao-Ming Zhang ORCID logo a  

* Corresponding authors

a State Key Laboratory of Applied Organic Chemistry & College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, China
E-mail: tuyq@lzu.edu.cn, zhangfm@lzu.edu.cn

b School of Chemistry and Chemical Engineering, Chongqing University, Chongqing 400044, China
E-mail: libs@cqu.edu.cn

c School of Chemistry & Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240, P. R. China

Abstract

A concise method of synthesizing the tetracyclic core of annotinolide C has been developed. The key steps include a tandem epoxidation/semipinacol rearrangement step to construct a quaternary aza [6.5] spiro ring (rings A and B), an intramolecular aldol reaction to assemble a [3.2.1] bridged ring system, and tandem semireduction/lactonization to form a five-membered lactone D-ring.

Graphical abstract: Construction of the tetracyclic core of the Lycopodium alkaloid annotinolide C

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Article information

DOI
https://doi.org/10.1039/D1QO00087J
Article type
Research Article
Submitted
18 Jan 2021
Accepted
11 Mar 2021
First published
17 Mar 2021

Org. Chem. Front., 2021,8, 2510-2514

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Construction of the tetracyclic core of the Lycopodium alkaloid annotinolide C

X. Guo, Y. Li, S. Wang, F. Zhang, B. Li, Y. Tu and X. Zhang, Org. Chem. Front., 2021, 8, 2510 DOI: 10.1039/D1QO00087J

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