The first enantioselective total synthesis of lantalucratin C and determination of its absolute configuration. Issue 38 (23rd September 2015)

• Record Type: Journal Article
• Authors: Ogata, Tokutaro; Tanaka, Manami; Ishigaki, Momoe; Shimizu, Maki; Nishiuchi, Arisa; Inamoto, Kiyofumi; Kimachi, Tetsutaro
• Is Part Of: Tetrahedron. Volume 71:Issue 38(2015)
• Page Start: 6672
• Page End: 6680
• Publication Date: 2015-09-23
• Subjects: Naphthoquinone -- Natural product -- Total synthesis -- Asymmetric epoxidation -- Oxidative cyclization; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2015.07.050
• Languages: English
• ISSNs: 0040-4020

Abstract

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 abstract: