Unusual, chemoselective etherification of 2-hydroxy-1,4-naphthoquinone derivatives utilizing alkoxymethyl chlorides: scope, mechanism and application to the synthesis of biologically active natural product (±)-lantalucratin C

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• 作者：Tokutaro Ogata ; ^&dagger ; ; ^{t-ogata@hokuriku-u.ac.jp" class="auth_mail" title="E-mail the corresponding author} ; Tomoyo Yoshida ; Maki Shimizu ; Manami Tanaka ; Chie Fukuhara ; Junko Ishii ; Arisa Nishiuchi ; Kiyofumi Inamoto ; Tetsutaro Kimachi ; ^{tkimachi@mukogawa-u.ac.jp" class="auth_mail" title="E-mail the corresponding author}
• 关键词：Naphthoquinone ; Etherification ; Protecting group ; Chemoselective ; Total synthesis
• 刊名：Tetrahedron
• 出版年：2016
• 出版时间：17 March 2016
• 年：2016
• 卷：72
• 期：11
• 页码：1423-1432
• 全文大小：1188 K

文摘

A novel etherification of 2-hydroxy-1,4-naphthoquinone derivatives with alkoxyalkyl chlorides and hydride bases is described. Precise study of the conditions and substrate scope suggested that the reaction occurs specifically in the molecule having a 2-hydroxy-1,4-benzoquinone skeleton. A chemoselective O-methylation reaction was achieved to afford a synthetically important intermediate, which offered easy access to a natural product possessing anti-tumor activity.