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

作者：Ogata Tokutaro^*; Yoshida Tomoyo; Shimizu Maki; Tanaka Manami; Fukuhara Chie; Ishii Junko; Nishiuchi Arisa; Inamoto Kiyofumi; Kimachi Tetsutaro^*

来源：Tetrahedron, 2016, 72(11): 1423-1432.

DOI：10.1016/j.tet.2016.01.040

• Naphthoquinone
• Etherification
• Protecting group
• Chemoselective
• Total synthesis

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.

• 出版日期2016-3-17