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

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

doi:10.1039/D0OB02399J

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

Weiwei Gao, Xiaodong Wang, Linbin Yao, Bencan Tang, Guohao Mu, Tao Shi, Zhen Wang

Department of Chemical and Environmental Engineering

Research output: Journal Publication › Article › peer-review

3 Citations (Scopus)

112 Downloads (Pure)

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.

Original language	English
Pages (from-to)	1748-1751
Journal	Organic & Biomolecular Chemistry
Volume	19
Issue number	8
DOIs	https://doi.org/10.1039/D0OB02399J
Publication status	Published - 28 Feb 2021

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10.1039/D0OB02399J

Synthesis of an isomer of lycoplanine Aviacascade cyclization to construct the spiro-N O-acetal moiety submitted versionAccepted author manuscript, 712 KBLicence: CC BY

http://dx.doi.org/10.1039/D0OB02399J

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title = "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.",

author = "Weiwei Gao and Xiaodong Wang and Linbin Yao and Bencan Tang and Guohao Mu and Tao Shi and Zhen Wang",

year = "2021",

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T1 - Synthesis of an isomer of lycoplanine a via cascade cyclization to construct the spiro-N,O-acetal moiety

AU - Gao, Weiwei

AU - Wang, Xiaodong

AU - Yao, Linbin

AU - Tang, Bencan

AU - Mu, Guohao

AU - Shi, Tao

AU - Wang, Zhen

PY - 2021/2/28

Y1 - 2021/2/28

N2 - 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.

AB - 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.

U2 - 10.1039/D0OB02399J

DO - 10.1039/D0OB02399J

M3 - Article

C2 - 33566055

SN - 1477-0520

VL - 19

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EP - 1751

JO - Organic & Biomolecular Chemistry

JF - Organic & Biomolecular Chemistry

IS - 8

ER -

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

Abstract

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