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Title: Construction of Quaternary Carbon Stereocenter of α-Tertiary Amine through Remote C-H Functionalization of Tris Derivatives: Enantioselective Total Synthesis of Myriocin
Authors: Miyagawa, Takashi
Inuki, Shinsuke
Oishi, Shinya
Ohno, Hiroaki
Author's alias: 井貫, 晋輔
大石, 真也
大野, 浩章
Issue Date: 9-Jul-2019
Publisher: American Chemical Society
Journal title: Organic Letters
Volume: 21
Issue: 14
Start page: 5485
End page: 5490
Abstract: We describe the development of a strategy for the construction of the quaternary carbon stereocenter of α-tertiary amines. This strategy highlights a site-selective C–H functionalization involving an alkoxy-radical-triggered 1, 5-hydrogen transfer (1, 5-HAT) reaction of a conformationally fixed spiro-compound derived from trishydroxymethylaminomethane (Tris). The utilization of this strategy enabled an enantioselective total synthesis of myriocin, a naturally occurring sphingosine analog that displays potent immunosuppressive activity.
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
The full-text file will be made open to the public on 9 July 2020 in accordance with publisher's 'Terms and Conditions for Self-Archiving'.
This is not the published version. Please cite only the published version. この論文は出版社版でありません。引用の際には出版社版をご確認ご利用ください。
DOI(Published Version): 10.1021/acs.orglett.9b01778
Appears in Collections:Journal Articles

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