- Synthesis and antimalarial activities of optically active labdane-type diterpenes
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An efficient method for the synthesis of optically active labdane-type diterpenes from (+)-manool 8 is described. We prepared the natural labdane-type diterpene 5 via key intermediate peroxide 9, and synthetic hydroxybutenolides 6 and 7 via a furan photosensitised oxygenation reaction of labdafuran (14). Compounds 5, 6, 7 and 9 were evaluated as inhibitors of the β-haematin formation and globin proteolysis, and then were assayed in a malarial murine model. Compound 9 was the most promising compound, showing a positive correlation between in vitro and in vivo activities.
- Villamizar, Jose,Pittelaud, Jean P.,Rodrigues, Juan R.,Gamboa, Neira,Canudas, Nieves,Tropper, Eleonora,Salazar, Franklin,Fuentes, Juan
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- Facile isolation of (E)-labda-8(17),12-diene-15,16-dial from Curcuma amada and its conversion to other biologically active compounds
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Curcuma amada Roxb. (Zingiberaceae) rhizomes have been found to be a good source of (E)-labda-8(17),12-diene- 15,16-dial. This has been chemically transformed to other biologically active compounds like aframodial, zerumin A as well as other natural products like (E)-labda-8(17),12-diene-15,16-olide, 15,16-epoxy-8(17),13(16),14-labdatriene and (-)- marginatone. The antimicrobial activity of zerumin A sodium salt as well as other derivatives of the dialdehyde has been established.
- Sheeja, Alan D. B.,Nair, Mangalam S.
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p. 319 - 324
(2014/05/06)
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- Facile access to labdane-type diterpenes: Synthesis of coronarin C, zerumin B, labda-8(17), 13(14)-dien-15,16-olide and derivatives from (+)-manool
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A practical method for the synthesis of optically active labdane-type diterpenes from (+)-manool 8, is described. We prepared the natural labdane-type diterpene 5 via key intermediate peroxide 9 and coronarin C 1, compound 8 and zerumin B 6 via a furan photosensitised oxygenation reactions.
- Villamizar, Jose E.,Juncosa, Jose,Pittelaud, Jean,Hernandez, Madeleyn,Canudas, Nieves,Tropper, Eleonora,Salazar, Franklin,Fuentes, Juan
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p. 342 - 346
(2008/02/12)
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- Synthesis of (+)-lagerstronolide from (+)-sclareol
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The γ-acetoxybutenolide (+)-lagerstronolide was synthesized from (+)-sclareol, with an overall yield of 10%. The absolute stereochemistry for the natural compound (-)-lagerstronolide has been correctly established.
- Basabe, Pilar,Bodero, Olga,Marcos, Isidro S.,Diez, David,de Román, Mónica,Blanco, Araceli,Urones, Julio G.
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p. 11838 - 11843
(2008/03/13)
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- SYNTHESIS OF LABDA-8(17),13(14)-DIENE-15,16-OLIDE AND 15,16-EPOXY-LABDA-8(17),13(16)-14-TRIENE AND THEIR REARRANGEMENT TO CLERODANE DERIVATIVES
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The title compounds 1b and 1c were synthesized from manool.On treatment with either trifluoroacetic acid or formic acid 1b provided in nearly 100percent yield 4a with a rearranged labdane skeleton.With sulfuric acid, however, 1b gave solely Δ8,9-isomer 5.Reduction of 4a with lithium diisobutylaluminium hydride afforded 4b.On treatment with sulfuric acid 4a reverted to 5.Rearrangement of the epoxide 6 with boron trifluoride-etherate led to a complex product mixture from wich no pure substance was obtained.
- Nakano, Tatsuhiko,Martin, Alfonso,Rojas, Anibal
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p. 1217 - 1219
(2007/10/02)
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