521-54-0

Basic information

• Product Name: galbulin
• Synonyms: galbulin;(1S)-1α-(3,4-Dimethoxyphenyl)-1,2,3,4-tetrahydro-6,7-dimethoxy-2β,3α-dimethylnaphthalene;1α-(3,4-Dimethoxyphenyl)-1,2,3,4-tetrahydro-6,7-dimethoxy-2β,3α-dimethylnaphthalene
• CAS NO: 521-54-0
• Molecular Formula: C₂₂H₂₈O₄
• Molecular Weight: 356.45532
• Mol File: 521-54-0.mol

Chemical Properties

• Boiling Point: 455.3°Cat760mmHg
• Flash Point: 114.8°C
• Appearance: /
• Density: 1.059g/cm³
• Vapor Pressure: 4.81E-08mmHg at 25°C
• Refractive Index: 1.528
• CAS DataBase Reference: galbulin(CAS DataBase Reference)
• NIST Chemistry Reference: galbulin(521-54-0)
• EPA Substance Registry System: galbulin(521-54-0)

Safety Data

• Hazardous Substances Data: 521-54-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C22H28O4/c1-13-9-16-11-20(25-5)21(26-6)12-17(16)22(14(13)2)15-7-8-18(23-3)19(10-15)24-4/h7-8,10-14,22H,9H2,1-6H3/t13-,14+,22+/m1/s1

Upstream product

• 59527-55-8 ditosylisolariciresinol dimethyl ether 
• 78178-23-1 dimesylisolariciresinol dimethyl ether 
• 528-63-2 veraguensin 
• 186581-53-3 diazomethane 
• 78341-26-1 (8R,7'S,8'S)-4,4'-dihydroxy-3,3'-dimethoxy-Δ^{1,3,5,1',3',5'} -8,8',6,7'-lignan 
• 119098-90-7 (8R,8R')-3,4,3',4'-tetramethoxylignan-9,9'-diyl bis(methanesulfonate) 
• 58311-18-5 (2R,3R)-2,3-bis[(3,4-dimethoxyphenyl)methyl]butane-1,4-diol 
• 21966-92-7 isolariciresinol dimethyl ether 
• 1360455-12-4 C₂₁H₂₆O₅ 
• 101205-05-4 C₂₂H₂₈O₅ 
• 1373333-26-6 (R)-4-benzyl-3-(3-(3,4-dimethoxyphenyl)propanoyl)-oxazolidin-2-one 
• 59527-55-8 ditosyl-β-conidendreol dimethyl ether 

Downstream Products

• 56433-90-0 6'-Bromogalbulin 
• 56433-91-1 (1R,2S,3R)-5-Bromo-1-(2-bromo-4,5-dimethoxy-phenyl)-6,7-dimethoxy-2,3-dimethyl-1,2,3,4-tetrahydro-naphthalene 
• 5811-91-6 1-(3,4-dimethoxy-phenyl)-6,7-dimethoxy-2,3-dimethyl-naphthalene 
• 6399-14-0 4α-(3,4-dimethoxyphenyl)-2α,3β-dimethyl-6,7-dimethoxy-1-tetralone 

Relevant articles and documents

NEOLIGNANS FROM NECTANDRA PUBERULA

The trunk wood of Nectandra puberula was found to contain 1,6-geranylgeranodioic acid besides five neoligands, the known veraguensin and the novel 7-hydroxy- and 7-oxo-3,4,3',4'-tetraoxy-8,8'-neolignans, all with the (8S,8'R-)-absolute configuration. Key Word Index--Nectandra puberula; Lauraceae; geranylgeranodioic acid; neolignans; diaryldimethyl-n-butanones.

Total synthesis of (+)-galbulin and unnatural lignans

The total synthesis of (+)-galbulin was achieved in 15% yield and 99% ee over eight steps from commercially available 4-veratraldehyde. The key steps include Meyer's asymmetric tandem addition to a chiral 2-oxazoline-substituted naphthalene, a Pd-catalyzed stereospecific decarboxylative γ-arylation, and a formal anti-Markovnikov hydromethylation. In addition, five unnatural lignans were synthesized using the same synthetic strategy.

Efficient Total Synthesis of (±)-Isoguaiacin and (±)-Isogalbulin

1-Arylnaphthalene lignans such as (-)-isoguaiacin and (-)-isogalbulin have been reported to exhibit notable biological properties. While (-)-isoguaiacin has not been previously synthesized, syntheses of (-)-isogalbulin are generally long and produce a mixture of stereoisomers. We herein present the efficient total synthesis of (±)-isoguaiacin and (±)-isogalbulin in seven and eight steps with an overall yield of 46% and 36%, respectively. The reported approach harnesses a hydrogenolysis reaction in acidic conditions, to convert a furan into an arylnaphthalen structure.

A practical total synthesis of (+)-isogalbulin and (+)-galbulin

A practical total synthesis of the natural products (+)-isogalbulin and (+)-galbulin has been achieved in 10 steps from readily available 3-(3,4-dimethoxyphenyl)propanoic acid. The total yields were 12.3% and 12.9%, respectively. The key steps involved Ev

Collective synthesis of several 2,7′-cyclolignans and their correlation by chemical transformations

Collective synthesis of anti-malarial 2,7′-cyclolignans has been stereoselectively achieved employing (±)-cyclogalgravin (2) as a linchpin through a series of functional group conversions, including redox reactions. Interestingly, 2 can be correlated with

Enantioselective total synthesis of (+)-galbulin via organocatalytic domino Michael-Michael-aldol condensation

A concise and practical enantioselective synthesis of (+)-galbulin has been achieved using organocatalytic domino Michael-Michael-aldol condensation and organocatalytic kinetic resolution as the key steps. The Royal Society of Chemistry 2012.

Acid-catalyzed cyclization of 2,3-dibenzylidenesuccinates: Synthesis of lignans (±)-cagayanin and (±)-galbulin

Acid-catalyzed cyclizations of E,E-dibenzylidenesuccinate esters have been developed as an efficient synthetic route to 1-aryl-1,2-dihydronaphthalenes. This reaction has been used in the synthesis of the naturally occurring lignans (±)-cagayanin and (±)-galbulin.

Ruthenium dioxide in fluoro acid medium V. Application to the non phenolic oxidative coupling of diarylbutanes. Conformational studies of cis and trans deoxyschizandrins

Ruthenium (IV) dioxide dihydrate in fluoro acidic medium was found to be a very efficient agent for the non phenolic oxidative coupling of diarylbutanes. We observed along with the expected aryl-aryl coupling, an unusual aryl-benzyl coupling, leading to a known class of lignans, the aryltetralins. Conformational studies of resultant cis and trans deoxyschizandrins were performed using high resolution NMR and molecular models.

THREE NEW LIGNANS FROM THE NUTMEG OF MYRISTICA CAGAYANESIS

The following constituents were isolated from the nutmeg of Myristica cagayanesis Merr.: trimyristin (1), otobain (2a), malabaricone A (3), otobanone (2b), cagayanin (4a), and cagayanone (4b).Compounds 2b, 4a and 4b are new lignans, and their structures were determined from spectral and chemical evidence.Keywords Myristica cagayanesis; nutmeg; lignan; otobanone; cagayanin; cagayanone

Oxidative Coupling of Lignans. II. Non-Phenolic Coupling of Diarylbutane Lignans Related to Matairesinol Dimethyl Ether

The non-phenolic oxidative coupling of some diarylbutane lignans related to matairesinol dimethyl ether (1) has been investigated.Coupling with a thallium(III) oxidant, prepared in situ from thallium(III) oxide and trifluoroacetic acid, converts these lig