Cyclohexenone Annelation by Alkylidene C−H Insertion:  Synthesis of Oxo-<i>T</i>-cadinol

and, Douglass F. Taber; Christos, Thomas E.; Hodge, C. Nicholas

doi:10.1021/jo951949k

Cited by 26 publications

(13 citation statements)

References 11 publications

(18 reference statements)

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“…9 The 1 H and 13 C NMR and DEPT data revealed that 9 had the skeleton of a cadinane type sesquiterpene. 8,9 Comparison of these data with those of 10R-hydroxyamorphane-4-en-3-one 8,10 indicated that the hydroxyl group of 10R-hydroxyamorphane-4-en-3-one was replaced by an O-methyl group in 9. This demonstrated that the methoxyl group was located at C-10, which was proved by an HMBC correlation between the methoxy protons and C-10.…”

Section: Resultsmentioning

confidence: 99%

Xanthone and Sesquiterpene Derivatives from the Fruits of Garcinia scortechinii

2005

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The fruits of Garcinia scortechinii afforded 10 new compounds: four caged-tetraprenylated xanthones (scortechinones Q−T, 1−4), four rearranged xanthones (scortechinones U−X, 5−8), and two sesquiterpene derivatives (scortechterpenes A, B, 9, 10), together with 14 known compounds: one sesquiterpene, two biflavonoids, and 11 caged-polyprenylated xanthones. Their structures were elucidated by analysis of spectroscopic data and comparison of the NMR data with those reported previously. All xanthone derivatives were evaluated for antibacterial activity against methicillin-resistant Staphylococcus aureus.

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Section: Resultsmentioning

confidence: 99%

Xanthone and Sesquiterpene Derivatives from the Fruits of Garcinia scortechinii

2005

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“…On the basis of the above evidence, compound 4 was determined to be 15-oxo-T-cadinol. By comparing the NMR data for compound 5 with that of reported data (Lin et al 1974;Taber et al 1996), the structure of 5 was determined as 3-oxo-T-cadinol. EIMS revealed compound 6 to be a sesquiterpene with molecular formula C 15 H 24 O 3 .…”

Section: Identification Of Cadinane-type Sesquiterpene Derivativesmentioning

confidence: 99%

Structure-activity relationships of cadinane-type sesquiterpene derivatives against wood-decay fungi

Chien

Wang

et al. 2005

Holzforschung

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Cadinane-type sesquiterpenes have a wide spectrum of biological activity, but their use as wood preservatives and the structure-activity relationships of their derivatives have not yet been reported. A total of 13 compounds were synthesized from T-cadinol, T-muurolol, and a-cadinol and their chemical structures were confirmed by IR, MS, and 1 H and 13 C NMR. The antifungal properties of 16 compounds against three wood-decay fungi were evaluated in vitro. a-Cadinol showed strong antifungal activity against Lenzites betulina, Trametes versicolor, and Laetiporus sulphureus (total mean IC 50 0.10 mM). Among the derivatives synthesized, 3b-ethoxy-T-muurolol (0.24 mM), 4jH-cadinan-10b-ol (0.25 mM), 4jH-muurolan-10b-ol (0.29 mM), and 4jH-cadinan-10a-ol (0.25 mM) showed good antifungal activity against all fungi tested. Correlation was observed between the antifungal activity of the compounds tested and log P. Furthermore, the presence of an unsaturated double bond and oxygen-containing functional groups in the compounds plays a key role in their antifungal activity. The stereo configuration of cadinane-type sesquiterpenes also influences their antifungal activity. Understanding how the structure of natural compounds relates to their antifungal function is important and may facilitate their application as novel wood preservatives.

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“…To increase the yield of the glyceraldehyde diacetate (3) and to avoid the formation of the hemiacetal (4), which could be promoted by the acidity of PCC, we carried out the reaction adding two equivalents of sodium acetate [ 80 ] ( Table 2 , entry 2) and it was found that decreasing the acidity of the medium promotes the accumulation of the aldehyde (3) with a consequent decrease in the reaction rate. Slow addition of 1,2-diacetin (2), and a higher solvent/PCC ratio ( Table 2 , entry 3), avoids the formation of ester (5); probably the low concentration of alcohol (2) slows the formation of hemiacetal (4) [ 78 ].…”

Section: Resultsmentioning

confidence: 99%

“…Slow addition of 1,2-diacetin (2), and a higher solvent/PCC ratio ( Table 2, entry 3), avoids the formation of ester (5); probably the low concentration of alcohol (2) slows the formation of hemiacetal (4) [78]. Accordingly, the best aldehyde proportions were obtained when the reaction was carried out adding only 1 equivalent of sodium acetate and simultaneously reducing the 1,2-diacetin (2) concentration by slow addition and high dilution ( To increase the yield of the glyceraldehyde diacetate (3) and to avoid the formation of the hemiacetal (4), which could be promoted by the acidity of PCC, we carried out the reaction adding two equivalents of sodium acetate [80] (Table 2, entry 2) and it was found that decreasing the acidity of the medium promotes the accumulation of the aldehyde (3) with a consequent decrease in the reaction rate. Slow addition of 1,2-diacetin (2), and a higher solvent/PCC ratio ( Table 2, entry 3), avoids the formation of ester (5); probably the low concentration of alcohol (2) slows the formation of hemiacetal (4) [78].…”

Section: 2-diacetin (2) Oxidation With Pccmentioning

confidence: 99%

Chemoenzymatic Synthesis of the New 3-((2,3-Diacetoxypropanoyl)oxy)propane-1,2-diyl Diacetate Using Immobilized Lipase B from Candida antarctica and Pyridinium Chlorochromate as an Oxidizing Agent

Plata

Ruiz

et al. 2020

IJMS

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To exploit the hydrolytic activity and high selectivity of immobilized lipase B from Candida antarctica on octyl agarose (CALB-OC) in the hydrolysis of triacetin and also to produce new value-added compounds from glycerol, this work describes a chemoenzymatic methodology for the synthesis of the new dimeric glycerol ester 3-((2,3-diacetoxypropanoyl)oxy)propane-1,2-diyl diacetate. According to this approach, triacetin was regioselectively hydrolyzed to 1,2-diacetin with CALB-OC. The diglyceride product was subsequently oxidized with pyridinium chlorochromate (PCC) and a dimeric ester was isolated as the only product. It was found that the medium acidity during the PCC treatment and a high 1,2-diacetin concentration favored the formation of the ester. The synthesized compounds were characterized using IR, MS, HR-MS, and NMR techniques. The obtained dimeric ester was evaluated at 100 ppm against seven bacterial strains and two Candida species to identify its antimicrobial activity. The compound has no inhibitory activity against the bacterial strains used but decreased C. albicans and C. parapsilosis growth by 49% and 68%, respectively. Hemolytic activity was evaluated, and the results obtained support the use of the dimeric ester to control C. albicans and C. parapsilosis growth in non-intravenous applications because the compound shows hemolytic activity.

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Cyclohexenone Annelation by Alkylidene C−H Insertion: Synthesis of Oxo-T-cadinol

Cited by 26 publications

References 11 publications

Xanthone and Sesquiterpene Derivatives from the Fruits of Garcinia scortechinii

Xanthone and Sesquiterpene Derivatives from the Fruits of Garcinia scortechinii

Structure-activity relationships of cadinane-type sesquiterpene derivatives against wood-decay fungi

Chemoenzymatic Synthesis of the New 3-((2,3-Diacetoxypropanoyl)oxy)propane-1,2-diyl Diacetate Using Immobilized Lipase B from Candida antarctica and Pyridinium Chlorochromate as an Oxidizing Agent

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