Novel Radical Cyclization Cascade for the Unified Synthesis of the Cedrane and Clovane Sesquiterpene Skeletons

Suzuki, Takahiro; Yamashita, Kotaro; Ikeda, Wataru; Ikeuchi, Kazutada; Tanino, Keiji

Novel Radical Cyclization Cascade for the Unified Synthesis of the Cedrane and Clovane Sesquiterpene Skeletons

Suzuki, Takahiro; Yamashita, Kotaro; Ikeda, Wataru et al.

Asian journal of organic chemistry, 2024, 13(9)

Permalink : https://hdl.handle.net/2115/96038

このアイテムのアクセス数:94件（2026-07-17 20:55 集計）

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アクセス権	open access
URI	https://hdl.handle.net/2115/96038
タイトル	Novel Radical Cyclization Cascade for the Unified Synthesis of the Cedrane and Clovane Sesquiterpene Skeletons
著者	Suzuki, Takahiro ; Yamashita, Kotaro ; Ikeda, Wataru ; Ikeuchi, Kazutada ; Tanino, Keiji
e-Rad_Researcher 80367052 著者名 Suzuki, Takahiro
著者名 Yamashita, Kotaro
著者名 Ikeda, Wataru
e-Rad_Researcher 70756676 著者名 Ikeuchi, Kazutada
e-Rad_Researcher 40217146 著者名 Tanino, Keiji
言語	英語
キーワード	Cyclization
	Cascade reactions
	Epoxides
	Radical reactions
	Sesquiterpenes
発行日	2024-09
出版者	Wiley-Blackwell
収録物名	Asian journal of organic chemistry
巻(号)	13(9)
抄録	Radical cyclization cascade reactions of epoxycyclohexanes possessing alkene and alkyne side chains have been achieved. Sequential 5- or 6-exo-trig/5-exo-dig reactions triggered by epoxide ring opening with Cp2TiCl were found to provide a useful unified synthetic method for generating the carbon skeletons of clovane and cedrane, two tricyclic sesquiterpenes. The factors responsible for the development of stereoselectivity during cyclization are also discussed. Radical cyclization cascade reactions of epoxycyclohexanes possessing alkene and alkyne side chains have been achieved. Sequential 5- or 6-exo-trig/5-exo-dig reactions triggered by epoxide ring opening with Cp2TiCl were found to provide a useful unified synthetic method for generating the tricyclic carbon skeletons of clovane and cedrane, which are used as fragrance ingredients and show various biological activities. image
資源タイプ	学術雑誌論文
出版タイプ	Accepted Manuscript
権利情報	This is the peer reviewed version of the following article: Novel Radical Cyclization Cascade for the Unified Synthesis of the Cedrane and Clovane Sesquiterpene Skeletons, which has been published in final form at https://doi.org/10.1002/ajoc.202400242. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions. This article may not be enhanced, enriched or otherwise transformed into a derivative work, without express permission from Wiley or by statutory rights under applicable legislation. Copyright notices must not be removed, obscured or modified. The article must be linked to Wiley’s version of record on Wiley Online Library and any embedding, framing or otherwise making available the article or pages thereof by third parties from platforms, services and websites other than Wiley Online Library must be prohibited.
PISSN	2193-5807
関連情報 (isVersionOf)	出版社版DOI https://doi.org/10.1002/ajoc.202400242