Facile and Simple Synthesis of Ring C Aromatic Diterpenes: Synthesis of (+)-13-Hydroxypodocarpa-8,11,13-triene and (+)-7-Deoxynimbidiol

Villamizar, José; Gamez, Carlos; Alcala, Antonio; Salazar, Franklin; Tropper, Eleonora; Angarita, Ana; Canudas, Nieves

doi:10.1080/00397911.2010.492078

Cited by 6 publications

(5 citation statements)

References 14 publications

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“…In our case, the 1 H NMR chemical shift of H-17a was observed at δ 4.49 and could be concluded for 13- epi -manool. Moreover, the specific rotation that we found in this study {[α] D 25 = +59.2 ( c 1.0, CHCl 3 )} also supported the identity as 13- epi- manool {[α] D 24 = +28 ( c 1.5, CHCl 3 for manool …”

Section: Resultssupporting

confidence: 82%

“…Moreover, the specific rotation that we found in this study {[α] D 25 = +59.2 (c 1.0, CHCl 3 )} also supported the identity as 13-epi-manool {[α] D 24 = +28 (c 1.5, CHCl 3 for manool. 49 The in vitro K&D system used in this study specifically quantified the mosquito biting-deterrent properties of Salvia essential oils and the pure compounds. Essential oils of S. leucantha (BDI value = 1.01) and S. elegans (BDI value = 0.87) showed biting-deterrent activity similar to that of DEET, whereas the activity of essential oils of S. off icinalis (BDI value = 0.63) and S. apiana (BDI value = 0.48) demonstrated low biting-deterrent activity against Ae.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…[α] D 25 = +59.2 (c 1.0, CHCl 3 ); 1 H NMR (500 MHz, CDCl 3 ) δ 0.99 (td, J = 13.5, 4.2 Hz, H-1a), 1.72 (H-1b), 1.46 (tt-like, J = 13.5, 3.5 Hz, H-2a), 1.55 (H-2b), 1.14 (td, J = 13.5, 4.1 Hz, H-3a), 1.37 (H-3b), 1.05 (dd, J = 12.6, 2.7 Hz, H-5), 1.28 (H-6a), 1.68 (H-6b), 1.94 (td, J = 13.0, 5.2 Hz, H-7b), 2.35 (br d, J = 13.0 Hz, H-7a), 1.53 (H-9), 1.30 (H-11a), 1.51 (H-11b), 1.22 (H-12a), 1.71 (H-12b), 5.88 (dd, J = 17.4, 10.7 Hz, H-14), 5.02 (d, J = 10.7 Hz, H-15a), 5.17 ( (7), 257 (43), 244 (9), 229 (6), 216 (6), 203 (11), 189 (19), 177 (20), 161 (16), 147 (15), 137 (87), 139 (23), 123 (45), 121 (41), 115 (6), 109 (52), 107 (54), 95 (92), 93 (68), 66 (45), 81 (100), 79 (69), 71 (40), 69 (71), 67 (49), 55 (59), 43 (42), 41 (61).…”

Section: Journal Of Agricultural and Food Chemistrymentioning

confidence: 99%

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Chemical Composition and Biological Activity of Four Salvia Essential Oils and Individual Compounds against Two Species of Mosquitoes

Alı

Tabanca

Demirci

et al. 2015

J. Agric. Food Chem.

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The chemical compositions of essential oils obtained from four species of genus Salvia were analyzed by gas chromatography with a flame ionization detector (GC-FID) and gas chromatography-mass spectrometry (GC-MS). The main compounds identified from Salvia species essential oils were as follows: 1,8-cineole (71.7%), α-pinene (5.1%), camphor (4.4%), and β-pinene (3.8%) in Salvia apiana; borneol (17.4%), β-eudesmol (10.4%), bornyl acetate (5%), and guaiol (4.8%) in Salvia elegans; bornyl acetate (11.4%), β-caryophyllene (6.5%), caryophyllene oxide (13.5%), and spathulenol (7.0%) in Salvia leucantha; α-thujene (25.8%), viridiflorol (20.4%), β-thujene (5.7%), and camphor (6.4%) in Salvia officinalis. In biting-deterrent bioassays, essential oils of S. leucantha and S. elegans at 10 μg/cm(2) showed activity similar to that of DEET (97%, N, N-diethyl-m-toluamide) in two species of mosquitoes, whereas the activities of S. officinalis and S. apiana essential oils were lower than those of the other oils or DEET. Pure compounds β-eudesmol and guaiol showed biting-deterrent activity similar to DEET at 25 nmol/cm(2), whereas the activity of 13-epi-manool, caryophyllene oxide, borneol, bornyl acetate, and β-caryophyllene was significantly lower than that of β-eudesmol, guaiol, or DEET. All essential oils showed larvicidal activity except that of S. apiana, which was inactive at the highest dose of 125 ppm against both mosquito species. On the basis of 95% CIs, all of the essential oils showed higher toxicity in Anopheles quadrimaculatus than in Aedes aegypti. The essential oil of S. leucantha with an LC50 value of 6.2 ppm showed highest toxicity in An. quadrimaculatus.

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Section: Resultssupporting

confidence: 82%

Section: ■ Results and Discussionmentioning

confidence: 99%

Section: Journal Of Agricultural and Food Chemistrymentioning

confidence: 99%

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Chemical Composition and Biological Activity of Four Salvia Essential Oils and Individual Compounds against Two Species of Mosquitoes

Alı

Tabanca

Demirci

et al. 2015

J. Agric. Food Chem.

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“…Villamizar and coworkers have recently reported the synthesis of 324 using Mn(III)-catalysed oxidation reaction as the key step for the acetylation of the C-H bond. 152 The synthesis employs readily available (+)-manool 321 as the starting material, which via a series of steps is converted into b-enone 322. Oxidation of b-enone 322 with Mn(OAc) 3 afforded the acetylated ketone 323 in 80% yield.…”

Section: Synthesis Of (+)-7-deoxynimbidiolmentioning

confidence: 99%

Recent advances in manganese(iii) acetate mediated organic synthesis

2013

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The preceding four decades have witnessed a major expansion in the field of free-radical assisted reactions, as they are becoming a key tool in organic, polymer and complex natural product chemistry. This progress has clearly changed the traditional idea of free-radical reactions being ''extremely uncontrollable'', thereby allowing chemists to deal with free radicals in a more accurate and controlled way.Manganese(III) acetate mediated radical reactions have reached distinction in this field, as a wide range of protocols involving manganese(III) acetate under mild and efficient reaction conditions have been developed for the synthesis of biologically active and important organic molecules through oxidation, addition and cyclization reactions, which are in general difficult to achieve by the established synthetic operations. The present review focuses on manganese(III) acetate mediated oxidative free-radical reactions that have been developed and adapted during the last five years. It includes the advancements made in the field of free-radical promoted carbon-carbon and carbon-oxygen bond forming reactions, illustrating the examples of furans, hydrofurans, pyrroles, bicyclic lactones, biaryls, oxepins, indole-alkaloids, 1,2benzanthracene and C 60 -fused tetrahydronaphthalene synthesis. Numerous manganese(III) acetate initiated carbon-phosphorus bond formation reactions were also devised during recent years, involving both phosphonyl and phosphinoyl radicals, and are a key part of this review. Manganese(III) acetate promotes functionalization of significant organic compounds, thereby guiding the synthesis of important and complex molecules, such as the formation of propellanes, quinolinones, 1,2-dioxalanes; oxidation of indoles; lactonization of fullerene [C 60 ], malonyl cyclopentanes, glycols; and hydroperoxidation of heterocycles. The review will also envelop several recent milestones that have been achieved in the chemistry of natural products pre ´cising the vital role of manganese(III) acetate in the key synthetic steps.

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“…In 2007, Jaiswal et al 22 suggested that (+)-totarol 19 may be useful as a lead compound to develop an effective antitubercular drug. The phenol (+)-13-hydroxypodocarpa-8,11,13-triene 20 was isolated from the bark of Taiwania cryptomeriodes in 2000 by Kuo et al 23 In 2010, Villamizar et al 24,25 reported the synthesis of (+)-nimbidiol 3, 7-deoxynimbidiol 5 and (+)-13-hydroxypodocarpa-8,11,13-triene 20 from (+)-manool 1 using the α,βunsaturated ketone 22 as a key intermediate (Scheme 6). The alcohol 1 was oxidised with anhydrous potassium permanganate in the presence of a phase transfer catalyst, trimethylphenylammonium chloride, to obtain ketone 6 in 90% yield.…”

Section: Ring C Aromatic Diterpenesmentioning

confidence: 99%

Use of (+)-manool in the Synthesis of Natural Products. Part II. Diterpenes and Relatives

Salazar

Villamizar

2013

Journal of Chemical Research

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Facile and Simple Synthesis of Ring C Aromatic Diterpenes: Synthesis of (+)-13-Hydroxypodocarpa-8,11,13-triene and (+)-7-Deoxynimbidiol

Cited by 6 publications

References 14 publications

Chemical Composition and Biological Activity of Four Salvia Essential Oils and Individual Compounds against Two Species of Mosquitoes

Chemical Composition and Biological Activity of Four Salvia Essential Oils and Individual Compounds against Two Species of Mosquitoes

Recent advances in manganese(iii) acetate mediated organic synthesis

Use of (+)-manool in the Synthesis of Natural Products. Part II. Diterpenes and Relatives

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