Title: The first enantioselective total synthesis of lantalucratin C and determination of its absolute configuration
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.
Publication Year: 2015
Publication Date: 2015-07-22
Language: en
Type: article
Indexed In: ['crossref']
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Cited By Count: 6
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