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.