Seven-Membered Lactam Derivatives of Podophyllotoxins as New Pesticidal Agents

Abstract As a continuation of our efforts to discover and develop natural-product-based insecticidal agents, three novel and unusual 7-membered lactam derivatives of podophyllotoxin were prepared by thionyl chloride-mediated ring-expanded Beckmann rearrangement. The steric configurations of 3a–c wer...

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Autores principales:	Xiaoyan Zhi, Yuanyuan Zhang, Jiulin Huang, Hui Xu
Formato:	article
Lenguaje:	EN
Publicado:	Nature Portfolio 2017
Materias:	Medicine R Science Q
Acceso en línea:	https://doaj.org/article/af3742d14df2442eb4706aec21840929
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spelling	oai:doaj.org-article:af3742d14df2442eb4706aec218409292021-12-02T16:06:19ZSeven-Membered Lactam Derivatives of Podophyllotoxins as New Pesticidal Agents10.1038/s41598-017-04136-32045-2322https://doaj.org/article/af3742d14df2442eb4706aec218409292017-06-01T00:00:00Zhttps://doi.org/10.1038/s41598-017-04136-3https://doaj.org/toc/2045-2322Abstract As a continuation of our efforts to discover and develop natural-product-based insecticidal agents, three novel and unusual 7-membered lactam derivatives of podophyllotoxin were prepared by thionyl chloride-mediated ring-expanded Beckmann rearrangement. The steric configurations of 3a–c were unambiguously identified by X-ray crystallography. It demonstrated that the configuration of the picropodophyllotoxin C4-oximes could also be confirmed by the corresponding C-ring expansion products via Beckmann rearrangement. Moreover, it was obviously further testified that when picropodophyllones reacted with hydroxylamine hydrochloride, only E configuration of picropodophyllotoxin C4-oximes was selectively produced. Compounds 3b and 3c showed more potent pesticidal activity than toosendanin against oriental armyworm, Mythimna separata (Walker).Xiaoyan ZhiYuanyuan ZhangJiulin HuangHui XuNature PortfolioarticleMedicineRScienceQENScientific Reports, Vol 7, Iss 1, Pp 1-8 (2017)
institution	DOAJ
collection	DOAJ
language	EN
topic	Medicine R Science Q
spellingShingle	Medicine R Science Q Xiaoyan Zhi Yuanyuan Zhang Jiulin Huang Hui Xu Seven-Membered Lactam Derivatives of Podophyllotoxins as New Pesticidal Agents
description	Abstract As a continuation of our efforts to discover and develop natural-product-based insecticidal agents, three novel and unusual 7-membered lactam derivatives of podophyllotoxin were prepared by thionyl chloride-mediated ring-expanded Beckmann rearrangement. The steric configurations of 3a–c were unambiguously identified by X-ray crystallography. It demonstrated that the configuration of the picropodophyllotoxin C4-oximes could also be confirmed by the corresponding C-ring expansion products via Beckmann rearrangement. Moreover, it was obviously further testified that when picropodophyllones reacted with hydroxylamine hydrochloride, only E configuration of picropodophyllotoxin C4-oximes was selectively produced. Compounds 3b and 3c showed more potent pesticidal activity than toosendanin against oriental armyworm, Mythimna separata (Walker).
format	article
author	Xiaoyan Zhi Yuanyuan Zhang Jiulin Huang Hui Xu
author_facet	Xiaoyan Zhi Yuanyuan Zhang Jiulin Huang Hui Xu
author_sort	Xiaoyan Zhi
title	Seven-Membered Lactam Derivatives of Podophyllotoxins as New Pesticidal Agents
title_short	Seven-Membered Lactam Derivatives of Podophyllotoxins as New Pesticidal Agents
title_full	Seven-Membered Lactam Derivatives of Podophyllotoxins as New Pesticidal Agents
title_fullStr	Seven-Membered Lactam Derivatives of Podophyllotoxins as New Pesticidal Agents
title_full_unstemmed	Seven-Membered Lactam Derivatives of Podophyllotoxins as New Pesticidal Agents
title_sort	seven-membered lactam derivatives of podophyllotoxins as new pesticidal agents
publisher	Nature Portfolio
publishDate	2017
url	https://doaj.org/article/af3742d14df2442eb4706aec21840929
work_keys_str_mv	AT xiaoyanzhi sevenmemberedlactamderivativesofpodophyllotoxinsasnewpesticidalagents AT yuanyuanzhang sevenmemberedlactamderivativesofpodophyllotoxinsasnewpesticidalagents AT jiulinhuang sevenmemberedlactamderivativesofpodophyllotoxinsasnewpesticidalagents AT huixu sevenmemberedlactamderivativesofpodophyllotoxinsasnewpesticidalagents
_version_	1718385045562982400

Seven-Membered Lactam Derivatives of Podophyllotoxins as New Pesticidal Agents

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