Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5214735 | Tetrahedron | 2015 | 9 Pages |
Abstract
Described here is the first enantioselective total synthesis of lantalucratin C, which was isolated from the rainforest plant Lantana involucrata, and which possesses anti-tumor activity. The OH group on the aromatic ring was systematically introduced by an appropriate management of the OH protecting groups. The alkyl side chain connected to a chiral carbon center was incorporated by directed ortho-lithiation of naphthalenes followed by asymmetric epoxidation. The furano-1,2-naphthoquinone skeleton was constructed from 3-hydroxyalkylnaphthalene by CAN-mediated oxidative cyclization. The absolute stereochemistry at the C2 carbon was assigned the R-configuration by the Kusumi-Mosher method.
Graphical abstractDownload full-size image
Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Tokutaro Ogata, Manami Tanaka, Momoe Ishigaki, Maki Shimizu, Arisa Nishiuchi, Kiyofumi Inamoto, Tetsutaro Kimachi,