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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. Issue 11 (17th March 2016)
Record Type:
Journal Article
Title:
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. Issue 11 (17th March 2016)
Main Title:
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
Abstract: 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. Graphical abstract: