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

Weiwei Gao | Zendy; Xiaodong Wang | Zendy; Linbin Yao | Zendy; Bencan Tang | Zendy; Guohao Mu | Zendy; Tao Shi | Zendy; Zhen Wang | Zendy

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

Author(s) -

Weiwei Gao,

Xiaodong Wang,

Linbin Yao,

Bencan Tang,

Guohao Mu,

Tao Shi,

Zhen Wang

Publication year - 2021

Publication title -

organic and biomolecular chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.923

H-Index - 146

eISSN - 1477-0539

pISSN - 1477-0520

DOI - 10.1039/d0ob02399j

Subject(s) - moiety , acetal , pentadecane , cascade , stereochemistry , chemistry , construct (python library) , cascade reaction , organic chemistry , computer science , catalysis , programming language , chromatography

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.

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