Synthesis of (.+-.)-umbelactone

Caine, Drury; Frobese, A. Stephen; Ukachukwu, Victoria C.

doi:10.1021/jo00153a025

Cited by 25 publications

(26 citation statements)

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“…The envisaged simultaneous hydrogenation of the γ,δ-olefinic linkage and cleavage of the benzyl group proved challenging. [29] Thus, standard hydrogenation procedures led within minutes to a mixture of the monohydrogenated compound 36, the saturated benzyl derivative 37, and the saturated alcohol 38. When the reaction was left for 10 min, only 38 was isolated in excellent yield (95 %) as a 1:1 mixture of epimers at C-1.…”

Section: Resultsmentioning

confidence: 99%

Synthetic Studies of Sesquiterpenes with the Dunniane Skeleton

Parés¹,

Alibés²,

Figueredo³

et al. 2012

Eur J Org Chem

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Section: Resultsmentioning

confidence: 99%

Synthetic Studies of Sesquiterpenes with the Dunniane Skeleton

Parés¹,

Alibés²,

Figueredo³

et al. 2012

Eur J Org Chem

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“…Then the ORs of selected compounds obtained with five employed functional were compared to the experimental data . After selecting the best functional B3LYP having the ability to reproduce experimental OR with the least error, the same protocol was applied to all selected compounds for the benchmarking of six basis sets, namely, 3‐21G, 6‐31G, aug‐cc‐pVDZ, aug‐cc‐pVTZ, DGDZVP, and DGDZVP2 were studied, which consisted of the following steps; 1) construction of 3D structures; 2) conformational search; 3) geometry optimization; 4) frequency calculations; 5) OR calculations.…”

Section: Methodsmentioning

confidence: 99%

Estimation of optical rotation of γ‐alkylidenebutenolide, cyclopropylamine, cyclopropyl‐methanol and cyclopropenone based compounds by a Density Functional Theory (DFT) approach

et al. 2017

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Computing the optical rotation of organic molecules can be a real challenge, and various theoretical approaches have been developed in this regard. A benchmark study of optical rotation of various classes of compounds was carried out by Density Functional Theory (DFT) methods. The aim of the present research study was to find out the best-suited functional and basis set to estimate the optical rotations of selected compounds with respect to experimental literature values. Six DFT functional LSDA, BVP86, CAM-B3LYP, B3PW91, and PBE were applied on 22 different compounds. Furthermore, six different basis sets, i.e., 3-21G, 6-31G, aug-cc-pVDZ, aug-cc-pVTZ, DGDZVP, and DGDZVP2 were also applied with the best-suited functional B3LYP. After rigorous effort, it can be safely said that the best combination of functional and basis set is B3LYP/aug-cc-pVTZ for the estimation of optical rotation for selected compounds.

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“…* sec-Butyl-lithium and t-butyl-lithium are also satisfactory. Methyl 5-chforotetronate (36). A solution of benzenesulphonyl chloride (0.64 g, 3.65 mmol) in dry T H F (4 ml) was added to the lithium salt (23) (made by procedure B) (3.33 mmol) stirred at -78 "C under nitrogen.…”

Section: Preparation Of 4-methoxy-2-( Trimethylsiloxy) Furanmentioning

confidence: 99%

“…Physical data and analyses for isomers (Wa) and (Wb) are given in Tables 9 and 10. Compound (!Ma) had peaks in the mass spectrum at m/z 202 (25%), 121 (loo), 118 (8), 113 (l), 90 (8), 77 (15), 69 (36), and 4 1 (2); and isomer (90b) had m/z 234 (0.6%), 202 (1 8), 12 1 (loo), 118 (3), 113 (3), 90 (3), 77 (23), 69 (24), and 41 (31). * See footnote * in Table 2.…”

Section: Preparation Of Compounds (84)-(86) Bjy Condensation Of (E)p-...mentioning

confidence: 99%

Synthetic routes to the piperolides, fadyenolides, epoxypiperolides, and related compounds

Pelter¹,

Al-Bayati²,

Ayoub³

et al. 1987

J. Chem. Soc., Perkin Trans. 1

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Syntheses of the piperolides, the fadyenolides, epoxypiperolide, and related compounds are described.( f ) -Narthogenin is also efficiently produced.From the Mexican plant Piper sanctum' we have previously isolated and characterised piperolide (l),' methylenedioxypiperolide (2),' ( + )-(7S,SS)-epoxypiperolide (3),'-" (-)-erythro-7,8-dihydro-7,8-dihydroxypiperolide (4),5 as well as a possible photoisomerisation product (5E)-piperolide (5),6*7 From Piper fudyenolii, indigenous to Jamaica, we have isolated and characterised similar butenolides, the fadyenolides (6) and (7).'These compounds are of particular interest for two reasons.First they are unique tetronates (derivatives of 4-hydroxybut-3-enolides) derived from higher plants rather than from fungal, microbial, or marine source^.^*^-'^ Secondly some of them, as well as certain of our synthetic products, have strong sedative as well as other most interesting physiological properties.It is tempting to speculate on a New World mutation in Piper species that leads from the usual pyrone derivatives such as kawain (8a)14 and methysticin (8b)14 produced by * We thank Dr. R. Pardasani for these experiments.

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Synthesis of (.+-.)-umbelactone

Abstract: Numerous physiologically active compounds contain an ,/3-butenolide system.1 2 34Umbelactone (la) is an example CH, QH, Br

Cited by 25 publications

References 1 publication

Synthetic Studies of Sesquiterpenes with the Dunniane Skeleton

Synthetic Studies of Sesquiterpenes with the Dunniane Skeleton

Estimation of optical rotation of γ‐alkylidenebutenolide, cyclopropylamine, cyclopropyl‐methanol and cyclopropenone based compounds by a Density Functional Theory (DFT) approach

Synthetic routes to the piperolides, fadyenolides, epoxypiperolides, and related compounds

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