- Total synthesis of (+)-galbulin and unnatural lignans
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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.
- Clausen, Florian,Studer, Armido
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supporting information
p. 6780 - 6783
(2020/09/15)
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- Efficient Total Synthesis of (±)-Isoguaiacin and (±)-Isogalbulin
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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.
- Pilkington, Lisa I.,Song, Soo Min,Fedrizzi, Bruno,Barker, David
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p. 1449 - 1452
(2017/07/22)
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- A practical total synthesis of (+)-isogalbulin and (+)-galbulin
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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
- Li, Xiaoyu,Jiao, Xiaozhen,Liu, Xiaoyu,Tian, Chengsen,Dong, Liang,Yao, Yangyang,Xie, Ping
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p. 6324 - 6327
(2015/02/19)
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- Collective synthesis of several 2,7′-cyclolignans and their correlation by chemical transformations
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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
- Peng, Yu,Luo, Zhen-Biao,Zhang, Jian-Jian,Luo, Long,Wang, Ya-Wen
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p. 7574 - 7586
(2013/11/06)
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- Enantioselective total synthesis of (+)-galbulin via organocatalytic domino Michael-Michael-aldol condensation
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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.
- Hong, Bor-Cherng,Hsu, Che-Sheng,Lee, Gene-Hsiang
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supporting information; experimental part
p. 2385 - 2387
(2012/03/27)
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- Acid-catalyzed cyclization of 2,3-dibenzylidenesuccinates: Synthesis of lignans (±)-cagayanin and (±)-galbulin
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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.
- Datta,Yau,Hooper,Yvon,Charlton
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p. 8606 - 8611
(2007/10/03)
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- Ruthenium dioxide in fluoro acid medium V. Application to the non phenolic oxidative coupling of diarylbutanes. Conformational studies of cis and trans deoxyschizandrins
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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.
- Dhal,Landais,Lebrun,Lenain,Robin
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p. 1153 - 1164
(2007/10/02)
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- THREE NEW LIGNANS FROM THE NUTMEG OF MYRISTICA CAGAYANESIS
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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
- Kuo, Yueh-Hsiung,Lin, Sheng-Tsair,Wu, Rong-En
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p. 2310 - 2312
(2007/10/02)
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- SYNTHESIS OF DIARYLBUTANES FROM CORDIGERINES AND REINVESTIGATION OF THEIR OXIDATIVE COUPLINGS IN DEOXYSCHIZANDRINS. - AN UNUSUAL FORMATION OF PHENYLTETRALIN LIGNANS -
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Dibenzylbutanolide lignans including cordigerines were synthetized and transformed in the corresponding diarylbutane lignans which were submitted to non-phenolic oxidative coupling conditions by using RuO2 or Tl2O3 in trifluoroacetic medium to give deoxyschizandrins.A concurently aryl-benzyl coupling leads to the formation of the corresponding phenyltetralin of which the structure was confirmed by total synthesis.
- Landais, Y.,Lebrun, A.,Lenain, V.,Robin, J.-P.
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p. 5161 - 5164
(2007/10/02)
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- New Reagent Systems Containing CrO3 Provide Precursors for Syntheses of Neo-lignans
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Oxidations of 1-aryl-1-propenes with new reagent systems, CrO3-HBF4-MeCN and CrO3-HClO4-MeCN, gave the 4-aryltetralones 1a and 1c, and the tetrahydrofuran 4, which are precursor molecules for aryltetrahydronaphthalene and tetrahydrofuran neo-lignans.Keywords - reagent system: chromium trioxide, neo-lignan; aryltetrahydronaphthalene; tetrahydrofuran
- Takeya, Tetsuya,Matsumoto, Hiroshi,Kotani, Eiichi,Tobinaga, Seisho
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p. 4364 - 4367
(2007/10/02)
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- New Reagent System containing CrO3 and Syntheses of Neo-lignans
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Oxidations of 1-arylprop-1-enes by the new reagent systems, CrO3-HBF4-MeCN or CrO3-HClO4-MeCN gave the 4-aryltetralones (1a) and (1c), and the tetrahydrofuran (3) which are precursor molecules for aryltetrahydronaphthalene and tetrahydrofuran neo-lignans.
- Takeya, Tetsuya,Kotani, Eiichi,Tobinaga, Seisho
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