- Total synthesis of (±)-joubertinamine from 3-(3,4-dimethoxyphenyl)- 5-bromo-2-pyrone
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The regioselective synthesis and Diels-Alder cycloaddition of 3-(3,4-dimethoxyphenyl)-5-bromo-2-pyrone provided a new efficient synthetic route to joubertinamine (9.6% total yield over 10 steps).
- Tam, Nguyen Thanh,Cho, Cheon-Gyu
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p. 3391 - 3392
(2008/02/12)
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- Opening of aryl-substituted epoxides to form quaternary stereogenic centers: Synthesis of (-)-mesembrine
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Cycloalkanones are easily converted into aryl-substituted cyclic alkenes by the addition of an aryl Grignard reagent followed by dehydration. These alkenes are good substrates for asymmetric epoxidation. We have found that the addition of allylic and benzylic Grignard reagents can occur preferentially at the benzylic position of the derived epoxides to give the quaternary stereogenic center. This approach led to a short synthesis of the nanomolar serotonin re-uptake inhibitor (-)-mesembrine.
- Taber, Douglass F.,He, Yigang
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p. 7711 - 7714
(2007/10/03)
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- A Synthesis of Seco-mesembrane Alkaloids, (+/-)-Joubertiamine, (+/-)-Joubertinamine, and (+/-)-Epijoubertinamine
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A synthesis of seco-mesembrane alkaloids, (+/-)-joubertiamine (4), (+/-)-joubertinamine (5), and (+/-)-epijoubertinamine (6), was accomplished starting with 2-allyl-2-aryl-5,5-ethylenedioxycyclohexanones (10 and 3), which are readily available by allylati
- Hoshino, Osamu,Ishizaki, Miyuki,Sawaki, Shohei,Yuasa, Masayuki,Umezawa, Bunsuke
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p. 3373 - 3380
(2007/10/02)
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- SCELETIUM (AIZOACEAE) ALKALOIDS: TOTAL SYNTHESIS OF RACEMIC MESEMBRANONE, JOUBERTINAMINE AND EPIJOUBERTINAMINE
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The total synthesis of the Sceletium alkaloids mesembranone, joubertinamine and epijoubertinamine via the intramolecular cyclization of an enone to a benzensulfonamide grouping under the conditions of a dissolving metal reduction is described.
- Sanchez, Ignacio H.,Soria, Jose de Jesus,Larraza, Maria Isabel,Flores, Humberto J.
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p. 551 - 554
(2007/10/02)
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- Total Syntheses of (+/-)-Mesembrine, (+/-)-Joubertinamine, and (+/-)-N-Demethylmesembrenone
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The syntheses of three members of the sceletium alkaloid family are developed from a common synthon, leading to short, high-yielding stereorational routes to (+/-)-mesembrine, (+/-)-joubertinamine, and (+/-)-N-demethylmesembrenone.The latter is synthesize
- Jeffs, Peter, W.,Redfearn, Richard,Wolfram, Joachim
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p. 3861 - 3863
(2007/10/02)
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