Synthesis of an isomer of lycoplanine a via cascade cyclization to construct the spiro-N,O-acetal moiety

Gao, Weiwei and Wang, Xiaodong and Yao, Linbin and Tang, Bencan and Mu, Guohao and Shi, Tao and Wang, Zhen (2021) Synthesis of an isomer of lycoplanine a via cascade cyclization to construct the spiro-N,O-acetal moiety. Organic & Biomolecular Chemistry, 19 (8). pp. 1748-1751. ISSN 1477-0520

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Abstract

An isomer of lycoplanine A with a 6/10/5/5 tetracyclic skeleton was synthesized using D–A reaction and cascasde reaction to respectively construct the [9.2.2] pentadecane skeleton and the challenging 1-oxa-6-azaspiro[4.4]nonane spirocenter. Morever, detailed DFT calculations were conducted to explain the selectivity in the D–A reaction. This study may provide sufficient experience for the total synthesis of lycoplanine A and other alkaloids with similar spiro-N,O-acetal cores.

Item Type: Article
Schools/Departments: University of Nottingham Ningbo China > Faculty of Science and Engineering > Department of Chemical and Environmental Engineering
Identification Number: https://doi.org/10.1039/D0OB02399J
Depositing User: Wang, Danni
Date Deposited: 24 Mar 2021 02:29
Last Modified: 24 Mar 2021 02:29
URI: http://eprints.nottingham.ac.uk/id/eprint/64854

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