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