Gmelanone

Last updated
Gmelanone
Gmelanone.png
Names
Preferred IUPAC name
(1R,2S,5S)-2,5-Di(2H-1,3-benzodioxol-5-yl)-3,6-dioxabicyclo[3.2.1]octan-8-one
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • InChI=1S/C20H16O7/c21-19-13-7-27-20(19,12-2-4-15-17(6-12)26-10-24-15)8-22-18(13)11-1-3-14-16(5-11)25-9-23-14/h1-6,13,18H,7-10H2/t13-,18-,20-/m1/s1
    Key: NNFGXXXVGRYOSF-CFSSXQINSA-N
  • O=C4[C@@H]1CO[C@]4(CO[C@@H]1c2ccc3OCOc3c2)c5ccc6OCOc6c5
Properties
C20H16O7
Molar mass 368.341 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Gmelanone is a lignan found in the heartwood of Gmelina arborea . [1] Arboreol can be transformed by acid catalysis into gmelanone. [2]

Related Research Articles

Muscimol Chemical compound

Muscimol is one of the principal psychoactive constituents of Amanita muscaria and related species of mushroom. Muscimol is a potent, selective agonist for the GABAA receptors and displays sedative-hypnotic, depressant and hallucinogenic psychoactivity. This colorless or white solid is classified as an isoxazole.

<i>Gmelina arborea</i> Species of flowering plant

Gmelina arborea,, locally known as gamhar, is a fast-growing deciduous tree in the family Lamiaceae.

Umbelliferone Chemical compound

Umbelliferone, also known as 7-hydroxycoumarin, hydrangine, skimmetine, and beta-umbelliferone, is a natural product of the coumarin family.

The Bischler–Napieralski reaction is an intramolecular electrophilic aromatic substitution reaction that allows for the cyclization of β-arylethylamides or β-arylethylcarbamates. It was first discovered in 1893 by August Bischler and Bernard Napieralski, in affiliation with Basle Chemical Works and the University of Zurich. The reaction is most notably used in the synthesis of dihydroisoquinolines, which can be subsequently oxidized to isoquinolines.

<i>Tetrahedron</i> (journal) Academic journal

Tetrahedron is a weekly peer-reviewed scientific journal covering the field of organic chemistry. According to the Journal Citation Reports, the journal has a 2014 impact factor of 2.641. Tetrahedron and Elsevier, its publisher, support an annual symposium. In 2010, complaints were raised over its high subscription cost.

Benzisoxazole Chemical compound

1,2-Benzisoxazole is an aromatic organic compound with a molecular formula C7H5NO containing a benzene-fused isoxazole ring structure. The compound itself has no common applications; however, functionalized benzisoxazoles and benzisoxazoyls have a variety of uses, including pharmaceutical drugs such as some antipsychotics (including risperidone, paliperidone, ocaperidone, and iloperidone) and the anticonvulsant zonisamide.

Hypoglycin A Chemical compound

Hypoglycin A is a naturally occurring amino acid derivative found in the unripened fruit of the Ackee tree and in the seeds of the box elder tree. It is toxic if ingested, and is the causative agent of Jamaican vomiting sickness. A 2017 Lancet report established a link between the consumption of unripened lychees resulting in hypoglycaemia and death from acute toxic encephalopathy.

The Étard reaction is a chemical reaction that involves the direct oxidation of an aromatic or heterocyclic bound methyl group to an aldehyde using chromyl chloride. For example, toluene can be oxidized to benzaldehyde.

The Woodward cis-hydroxylation is the chemical reaction of alkenes with iodine and silver acetate in wet acetic acid to form cis-diols.(conversion of olefin into cis-diol)

Pivalic acid is a carboxylic acid with a molecular formula of (CH3)3CCO2H. This colourless, odiferous organic compound is solid at room temperature. A common abbreviation for the pivalyl or pivaloyl group (t-BuC(O)) is Piv and for pivalic acid (t-BuC(O)OH) is PivOH.

Nucleoside phosphoramidite

Nucleoside phosphoramidites are derivatives of natural or synthetic nucleosides. They are used to synthesize oligonucleotides, relatively short fragments of nucleic acid and their analogs. Nucleoside phosphoramidites were first introduced in 1981 by Beaucage and Caruthers. To avoid undesired side reactions, reactive hydroxy and exocyclic amino groups present in natural or synthetic nucleosides are appropriately protected. As long as a nucleoside analog contains at least one hydroxy group, the use of the appropriate protecting strategy allows one to convert that to the respective phosphoramidite and to incorporate the latter into synthetic nucleic acids. To be incorporated in the middle of an oligonucleotide chain using phosphoramidite strategy, the nucleoside analog must possess two hydroxy groups or, less often, a hydroxy group and another nucleophilic group (amino or mercapto). Examples include, but are not limited to, alternative nucleotides, LNA, morpholino, nucleosides modified at the 2'-position (OMe, protected NH2, F), nucleosides containing non-canonical bases (hypoxanthine and xanthine contained in natural nucleosides inosine and xanthosine, respectively, tricyclic bases such as G-clamp, etc.) or bases derivatized with a fluorescent group or a linker arm.

Mosher's acid, or α-methoxy-α-trifluoromethylphenylacetic acid (MTPA) is a carboxylic acid which was first used by Harry Stone Mosher as a chiral derivatizing agent. It is a chiral molecule, consisting of R and S enantiomers.

Neoflavonoids are a class of polyphenolic compounds. While flavonoids have the 2-phenylchromen-4-one backbone, neoflavonoids have the 4-phenylchromen backbone with no hydroxyl group substitution at position 2.

The Abramov reaction is the related conversions of trialkyl to α-hydroxy phosphonates by the addition to carbonyl compounds. In terms of mechanism, the reaction involves attack of the nucleophilic phosphorus atom on the carbonyl carbon. It was named after the Russian chemist Vasilii Semenovich Abramov (1904–1968) in 1957.

Arboreol Chemical compound

Arboreol is an epoxylignan.

Gummadiol Chemical compound

Gummadiol is a lignan hemiacetal. It can be isolated from the heartwood of Gmelina arborea.

Gmelinol Chemical compound

Gmelinol is a lignan. (+)-Gmelinol can be isolated from the heartwood of Gmelina arborea. This compound, along with four other chemicals also found in the same species, (+)-7′-O-ethyl arboreol, (+)-paulownin, (+)-epieudesmin and (−)-β-sitosterol, shows antifungal activity against Trametes versicolor.

The Chan–Lam coupling reaction – also known as the Chan–Evans–Lam coupling is a cross-coupling reaction between an aryl boronic acid and an alcohol or an amine to form the corresponding secondary aryl amines or aryl ethers, respectively. The Chan–Lam coupling is catalyzed by copper complexes. It can be conducted in air at room temperature. The more popular Buchwald–Hartwig coupling relies on the use of palladium.

Ganugapati Sree Rama Subba Rao is an Indian natural product chemist and a former chair of the department of sciences at the Indian Institute of Science (IISc). He is known for his researches on dihydroaromatics obtained through Birch reduction of aromatic compounds and is an elected fellow of the Indian National Science Academy, and the Indian Academy of Sciences. The Council of Scientific and Industrial Research, the apex agency of the Government of India for scientific research, awarded him the Shanti Swarup Bhatnagar Prize for Science and Technology, one of the highest Indian science awards, in 1982, for his contributions to chemical sciences.

1,2-Dioxolane Chemical compound

1,2-Dioxolane is a chemical compound with formula C
3
H
6
O
2
, whose molecule has a ring of three carbon atoms and two oxygen atoms in adjacent positions. Its structural formula could be written as [–(CH
2
)3–O–O–].

References

  1. Anjaneyulu, A.S.R.; Rao, A.Madhusudhana; Rao, V.Kameswara; Row, L.Ramachandra; Pelter, Andrew; Ward, Robert S. (1977). "Novel hydroxy lignans from the heartwood of gmelina arborea". Tetrahedron. 33: 133–143. doi:10.1016/0040-4020(77)80444-4.
  2. Ramachandra Row, L.; Ventkateswarlu, Reveru; Pelter, Andrew; Ward, Robert S. (1980). "Acid catalysed rearrangements of arboreol: A biomimetic synthesis of gmelanone". Tetrahedron Letters. 21 (30): 2919. doi:10.1016/S0040-4039(00)78645-X.