Issue 8, 2021

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

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.

Graphical abstract: Synthesis of an isomer of lycoplanine A via cascade cyclization to construct the spiro-N,O-acetal moiety

Supplementary files

Article information

Article type
Communication
Submitted
02 Dec 2020
Accepted
02 Feb 2021
First published
02 Feb 2021

Org. Biomol. Chem., 2021,19, 1748-1751

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

W. Gao, X. Wang, L. Yao, B. Tang, G. Mu, T. Shi and Z. Wang, Org. Biomol. Chem., 2021, 19, 1748 DOI: 10.1039/D0OB02399J

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