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Issue 3, 2019
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A novel approach to oxazole-containing diterpenoid synthesis from plant roots: salviamines E and F

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Abstract

In this study, salviamines E and F, which are structurally unique abietane-type diterpene alkaloids containing an oxazole ring, were efficiently synthesized from a known molecule, 5,7,8-trimethoxy-1-naphthol. The synthetic sequence involves the following crucial steps: (i) the assembly of a carbon skeleton by coupling a six-carbon homoprenyl unit with a naphthalene moiety (Kumada–Tamao–Corriu coupling); (ii) the construction of a tricyclic phenanthrene ring by acid-induced cyclization of a naphthalene derivative with a homoprenyl side chain; (iii) the formation of an oxazole ring by nucleophilic ring closure of a 2-aminophenylene-1,4-diyl-diformate or -diacetate moiety and (iv) Friedel–Crafts acetylation at the C13 position of the tetracyclic intermediates to obtain the two target molecules, salviamines E and F. To the best of our knowledge, salviamine synthesis is reported here for the first time.

Graphical abstract: A novel approach to oxazole-containing diterpenoid synthesis from plant roots: salviamines E and F

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Publication details

The article was received on 05 Dec 2018, accepted on 16 Dec 2018 and first published on 18 Dec 2018


Article type: Paper
DOI: 10.1039/C8OB03030H
Citation: Org. Biomol. Chem., 2019,17, 655-663
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    A novel approach to oxazole-containing diterpenoid synthesis from plant roots: salviamines E and F

    K. Narita, N. Fujisaki, Y. Sakuma and T. Katoh, Org. Biomol. Chem., 2019, 17, 655
    DOI: 10.1039/C8OB03030H

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