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Synthesis of a Bicyclo[2.2.1]heptane Skeleton with Two Oxy-Functionalized Bridgehead Carbons via the Diels-Alder Reaction

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Please use this identifier to cite or link to this item:http://hdl.handle.net/2115/87387

Title: Synthesis of a Bicyclo[2.2.1]heptane Skeleton with Two Oxy-Functionalized Bridgehead Carbons via the Diels-Alder Reaction
Authors: Ikeuchi, Kazutada Browse this author →KAKEN DB
Sasage, Tomonari Browse this author
Yamada, Gen Browse this author
Suzuki, Takahiro Browse this author
Tanino, Keiji Browse this author
Issue Date: 3-Dec-2021
Publisher: American Chemical Society
Journal Title: Organic letters
Volume: 23
Issue: 23
Start Page: 9123
End Page: 9127
Publisher DOI: 10.1021/acs.orglett.1c03451
Abstract: We describe a synthetic method for a bicyclo[2.2.1]heptane skeleton with two oxy-functionalized bridgehead carbons. This method involves an intermolecular Diels-Alder reaction using 5,5-disubstituted 1,4-bis(silyloxy)-1,3-cyclopentadienes, the diene structure of which has never been synthesized. Furthermore, the intramolecular Diels-Alder reaction using a diene bearing a dienophile moiety at the C-S position can provide a tricyclic carbon framework that includes the bicyclo[2.2.1]heptane skeleton. The novel bicyclo[2.2.1]heptane derivatives could be utilized as versatile building blocks for organic synthetic chemistry.
Rights: This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://pubs.acs.org/articlesonrequest/AOR-U5BQPGRJGS3A2VSFYEVW.
Type: article (author version)
URI: http://hdl.handle.net/2115/87387
Appears in Collections:理学院・理学研究院 (Graduate School of Science / Faculty of Science) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

Submitter: 池内 和忠

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