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Title: A short synthesis of (+)-β-lycorane by asymmetric conjugate addition cascade
Authors: Nishimura, Katsumi
Fukuyama, Naoshi
Yasuhara, Tomohisa
Yamashita, Mitsuaki
Sumiyoshi, Takaaki
Yamamoto, Yasutomo
Yamada, Ken-ichi
Tomioka, Kiyoshi
Author's alias: 山田, 健一
富岡, 清
Keywords: Chiral ligand
Asymmetric synthesis
Organolithiums
Conjugate addition
Lycorane
Issue Date: 30-Sep-2015
Publisher: Elsevier Ltd.
Journal title: Tetrahedron
Volume: 71
Issue: 39
Start page: 7222
End page: 7226
Abstract: The chiral diether ligand-controlled asymmetric conjugate addition of organolithiums to nona-2, 7-dienedioate and subsequent intramolecular conjugate addition of the enolate intermediate gave all-trans trisubstituted cyclohexanes with high ee and yields. Using this methodology, an efficient short asymmetric total synthesis of (+)-β-lycorane was accomplished in 33% overall yield through five steps from the dienedioate.
Rights: © 2015. This manuscript version is made available under the CC-BY-NC-ND 4.0 license http://creativecommons.org/licenses/by-nc-nd/4.0/
The full-text file will be made open to the public on 30 September 2017 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。
URI: http://hdl.handle.net/2433/201854
DOI(Published Version): 10.1016/j.tet.2015.03.014
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