- An Acid-Catalyzed Epoxide Ring-Opening/Transesterification Cascade Cyclization to Diastereoselective Syntheses of (±)-β-Noscapine and (±)-β-Hydrastine
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An acid-catalyzed stereoselective epoxide ring-opening/intramolecular transesterification cascade cyclization reaction and N-Boc deprotection was found to be a successful strategy to construct the phthalide tetrahydroisoquinoline skeleton in one pot. Based on this strategy, the unified and highly diastereoselective routes for the total syntheses of (±)-β-Noscapine and (±)-β-Hydrastine were exploited.
- Li, Jihui,Liu, Yongxiang,Song, Xinjing,Wu, Tianxiao,Meng, Jiaxin,Zheng, Yang,Qin, Qiaohua,Zhao, Dongmei,Cheng, Maosheng
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p. 7149 - 7153
(2019/09/30)
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- A new total synthesis of (±)-α-noscapine
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A new, convergent total synthesis of (±)-α-noscapine was developed on a grams scale through the condensation of 3-trimethylsilyl-meconin derivative 9 and the iodized salt cotarnine derivative 20 as the key step. Staring from simple 2,3-dimethoxybenzoic acid, piperonal and 2,2-dimethoxyethanamine, through the traditional chemical processes to give the final product in 11.6% yield over 14 steps.
- Mao, Yongjun,Song, Shuai,Zhao, Dongmei,Cheng, Maosheng
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p. 2633 - 2640
(2014/01/06)
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- Blocking group-directed diastereoselective total synthesis of (±)-α-noscapine
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A new approach for the diastereoselective synthesis of (±)-α- noscapine, a phthalide tetrahydroisoquinoline alkaloid exhibiting several biological activities, is described. The strategy features a blocking group-directed Bischler-Napieralski reaction followed by diastereoselective reduction (α/β>23:1). One of the key intermediates, phthalide-3-carboxylic acid, could be efficiently prepared from simple benzoic acid derivative and glyoxylic acid in one-pot.
- Ni, Jizhi,Xiao, Heping,Weng, Lipeng,Wei, Xiaofeng,Xu, Youjun
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p. 5162 - 5167
(2011/07/31)
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- TOTAL SYNTHESIS OF (+/-)-α-NARCOTINE VIA BISCHLER-NAPIERALSKI CYCLIZATION
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Refinement of the synthesis of the phthalideisoquinoline alkaloid (+/-)-α-narcotine by Bischler-Napieralski reaction is discussed.The total synthesis of (+/-)-α-narcotine and its "unnatural" regioisomer has been completed.
- Varga, Zsofia,Blasko, Gabor,Doernyei, Gabor,Szantay, Csaba
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p. 831 - 837
(2007/10/02)
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- Novel Zinc-Promoted Alkylation of Iminium Salts. New Synthesis of Benzylisoquinoline, Phthalidylisoquinoline, and Protoberberine Alkaloids and Related Compounds
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Zinc-promoted reductive coupling reaction of iminium salts with alkyl halides was found to be a successful key reaction for synthesis of a variety of alkaloids such as benzylisoquinoline, phthalidylisoquinoline, and protoberberine alkaloids.More specifically, laudanosine, cordrastine, hydrastine, narcotine, tetrahydropalmatine, and canadine were obtained.A new route for the synthesis of the emetine and yohimbine skeletons was exploited.
- Shono, Tatsuya,Hamaguchi, Hiroshi,Sasaki, Manji,Fujita, Shumei,Nagami, Kimihiko
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p. 1621 - 1628
(2007/10/02)
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