Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5217500 | Tetrahedron | 2013 | 7 Pages |
Abstract
The first total synthesis of (±)-lantalucratins A and B is described. Introduction of an alkyl side chain at the 6-position was proceeded by directed ortho-lithiation and subsequent alkylation reaction to afford 6-alkyl-5,7,8-trimethoxy-1-naphthol as a synthetically important intermediate for (±)-lantalucratins A and B in excellent yield with complete regioselectivity. The 1,2-naphthoquinone fused five-membered cyclic ether framework was constructed directly from 3-hydroxyalkyl-naphthalenes by oxidative intramolecular cyclization reaction with diammonium cerium(IV) nitrate. (±)-Lantalucratins A and B were obtained in 69% and 45% overall yields, respectively.
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Authors
Tokutaro Ogata, Yoshiko Sugiyama, Saki Ito, Kazuha Nakano, Eri Torii, Arisa Nishiuchi, Tetsutaro Kimachi,