Abstract: Retro-Diels-Alder decomposition of dodecahydro-endo-4b,12-ethenochrysene-1,4-diones obtained from a tricyclic diterpenoid, levopimaric acid, gave optically active 5-[2-(6-vinyl-2,6-dimethyl-2-carboxycyclohexyl) ethyl]-7-isopropyl-1,4-naphthoquinones which reacted with silyloxybutadienes to produce the corresponding 6- and 7-hydroxyanthraquinones, 5-furyl-7-hydroxytetrahydroanthraquinones, or 5-furyl-7-oxohexahydroanthraquinones. Condensation of the naphthoquinone derivatives with 5-isopropenyl-2,3-dihydrothiophene 1,1-dioxide resulted in the formation of 6,11-dioxodihydro- and 6,11-dioxohexahydroanthra[2,1-b]thiophene 3,3-dioxides. 6- and 7-Hydroxyanthraquinones were also obtained by reaction of dodecahydro-endo-4b,12-ethenochrysene-1,4-diones with Danishevsky diene, followed by cleavage of the polycyclic adducts. The cycloaddition of 5-[2-(-2-carboxy-2,6-dimethyl-6-vinylcyclohexyl)ethyl]-7-isopropyl-1,4-naphthoquinones in the presence of Lewis acids was characterized by increased regioselectivity.

Cite: Shul'ts E.E. , Oleinikov D.S. , Nechepurenko I.V. , Shakirov M.M. , Tolstikov G.A.
Synthetic transformations of higher terpenoids: XVIII. Synthesis of optically active 9,10-anthraquinone derivatives
Russian Journal of Organic Chemistry. 2009. V.45. N1. P.102-114. DOI: 10.1134/S1070428009010138 WOS Scopus РИНЦ

Dates:

Published print:	Jan 1, 2009
Published online:	Feb 17, 2009

Identifiers:

Web of science	WOS:000263507800013
Scopus	2-s2.0-60849127889
Elibrary	13603221
OpenAlex	W2049279540

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