- Asymmetric Total Synthesis and Biological Evaluation of (+)-Cycloclavine
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The first total synthesis of natural (+)-cycloclavine uses a catalytic asymmetric cyclopropanation of allene, a regiospecific Pd-catalyzed enone formation, and two intramolecular Diels-Alder reactions for indole/indoline annulations. The binding properties of natural (+)- and unnatural (-)-cycloclavine on 16 CNS receptors revealed significant stereospecificity and unique binding profiles in comparison to LSD, psilocin, and DMT. Differential 5-HT affinities, as well as novel sigma1 receptor properties bode well for potential therapeutic developments of clavine alkaloid scaffolds.
- McCabe, Stephanie R.,Wipf, Peter
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- Benzoannellated Fenestranes Bearing para-Terphenyl Units
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The synthesis of several centrotriindanes bearing ortho-phenyl groups in the sterically constricted bay regions is described. The classical three-step sequence including twofold cyclodehydration of the corresponding 2,2-dibenzyl-1,3-indanediols afforded a
- Seifert, Monika,Barth, Dieter,Kuck, Dietmar
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p. 6435 - 6449
(2021/11/30)
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- Synthesis and Structure of a Functionalized [9]Cycloparaphenylene Bearing Three Indeno[2,1-a]fluorene-11,12-dione-2,9-diyl Units
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A synthetic pathway to a functionalized [9]cycloparaphenylene bearing three indeno[2,1-a]fluorene-11,12-dione-2,9-diyl units in the macrocyclic ring structure ([3]CIFO) has been developed. The 1H and 13C NMR spectra show that only the anti rotamer (anti-[3]CIFO) is produced. DFT calculations indicate that the anti rotamer is thermodynamically more stable than the syn rotamer by 4.3 kcal/mol, and the rotational barrier from the anti to syn rotamer is estimated to be 23.3 kcal/mol. The UV-vis and fluorescence spectra and cyclic voltammogram of anti-[3]CIFO were investigated.
- Li, Shuangjiang,Aljhdli, Merfat,Thakellapalli, Haresh,Farajidizaji, Behzad,Zhang, Yu,Akhmedov, Novruz G.,Milsmann, Carsten,Popp, Brian V.,Wang, Kung K.
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supporting information
p. 4078 - 4081
(2017/08/15)
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- (2,1-a)-Indenofluorene derivatives: Syntheses, X-ray structures, optical and electrochemical properties
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Two novel fluorophores based on the (2,1-a)-indenofluorenyl backbone, dispiro[fluorene-9,11'-indeno[2,1-a]fluorene-12',9''-fluorene], (2,1-a)-DSF-IF and 11,12-dihydroindeno[2,1-a]fluorene (2,1-a)-IF have been prepared through original and efficient synthe
- Thirion, Damien,Poriel, Cyril,Rault-Berthelot, Joelle,Barriere, Frederic,Jeannin, Olivier
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supporting information; experimental part
p. 13646 - 13658
(2011/02/27)
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- 4,7-Diphenylisobenzofuran: A useful intermediate for the construction of phenyl-substituted acenes
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(Chemical Equation Presented) The formation and subsequent reactivity of previously unknown 4,7-diphenylisobenzofuran, 5, is reported. The Diels-Alder reaction between 5 and p-benzoquinone in boiling glacial acetic acid yields an unprecedented exo,exo ant
- Rainbolt, James Eric,Miller, Glen P.
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p. 3020 - 3030
(2007/10/03)
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