- Stereocontrolled Total Synthesis of (-)-Picrotoxinin and (+)-Coriamyrtin via a Common Isotwistane Intermediate
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Stereocontrolled total synthesis of (-)-picrotoxinin (1) and (+)-coriamyrtin (2), toxic sesquiterpenoids of plant origin, is described, utilizing isotwistane compounds as common and key intermediates.
- Niwa, Haruki,Wakamatsu, Kazumasa,Hida, Tsuneaki,niiyama, Kenji,Kigoshi, Hideo,et al.
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- Synthesis of (-)-Picrotoxinin by Late-Stage Strong Bond Activation
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We report a concise, stereocontrolled synthesis of the neurotoxic sesquiterpenoid (-)-picrotoxinin (1, PXN). The brevity of the route is due to regio-and stereoselective formation of the [4.3.0] bicyclic core by incorporation of a symmetrizing geminal dim
- Burdge, Hannah E.,Crossley, Steven W. M.,Lambrecht, Michael J.,Shenvi, Ryan A.,Tong, Guanghu
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- SHORT SYNTHESES OF (-)-PICROTOXININ AND RELATED COMPOUNDS
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The present disclosure relates to concise processes for making (?)-picrotoxinin (1, PXN) and 5-methyl-picrotoxinin (20, 5MePXN), and to 5MePXN, its pharmaceutical compositions, and its method of use for inhibiting GABAA receptor.
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- Palladium-catalyzed enyne cycloisomerization reaction in an asymmetric approach to the picrotoxane sesquiterpenes. 2. Second-generation total syntheses of corianin, picrotoxinin, picrotin, and methyl picrotoxate
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An alternative, more efficient synthesis of the picrotoxane core by palladium-catalyzed cycloisomerization of an enyne requires the design of a new catalyst system based upon 1,3-bis(dibenzophospholyl)propane and 2- (diphenylphosphino)benzoic acid as liga
- Trost, Barry,Krische, Michael J.
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p. 6131 - 6141
(2007/10/03)
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- Stereoselective Total Synthesis of (-)-Picrotoxnin and (-)-Picrotin
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The stereoselective total synthesis of (-)-picritoxnin (1) and (-)-picrotin (2), starting from (+)-5β-hydroxycarvone (3), is described.Eight contiguous asymmetric centers on a cis-fused hydrindane ring system were stereoselectively prepared via three key
- Miyashita, Masaaki,Suzuki, Toshio,Yoshikoshi, Akira
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p. 3728 - 3734
(2007/10/02)
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