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

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 chemoselec...

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Bibliographic Details
Published in:Tetrahedron 2016-03, Vol.72 (11), p.1423-1432
Main Authors: Ogata, Tokutaro, Yoshida, Tomoyo, Shimizu, Maki, Tanaka, Manami, Fukuhara, Chie, Ishii, Junko, Nishiuchi, Arisa, Inamoto, Kiyofumi, Kimachi, Tetsutaro
Format: Article
Language:English
Subjects:
Chemoselective
Etherification
Naphthoquinone
Protecting group
Total synthesis
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Summary: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. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2016.01.040