10421-76-8Relevant academic research and scientific papers
Blocking group-directed diastereoselective total synthesis of (±)-α-noscapine
Ni, Jizhi,Xiao, Heping,Weng, Lipeng,Wei, Xiaofeng,Xu, Youjun
, p. 5162 - 5167 (2011)
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.
A new total synthesis of (±)-α-noscapine
Mao, Yongjun,Song, Shuai,Zhao, Dongmei,Cheng, Maosheng
, p. 2633 - 2640 (2013)
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.
An Acid-Catalyzed Epoxide Ring-Opening/Transesterification Cascade Cyclization to Diastereoselective Syntheses of (±)-β-Noscapine and (±)-β-Hydrastine
Li, Jihui,Liu, Yongxiang,Song, Xinjing,Wu, Tianxiao,Meng, Jiaxin,Zheng, Yang,Qin, Qiaohua,Zhao, Dongmei,Cheng, Maosheng
, p. 7149 - 7153 (2019/09/30)
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.
NARCOTINE PURIFICATION PROCESS
-
Page/Page column 6-11, (2008/06/13)
A process for purifying Narcotine to remove color and impurities to form Noscapine. The process includes forming an aqueous isopropanol solution with the Narcotine product wherein the isopropanol concentration of the solution is about 20% to about 70% by volume; and adjusting the pH of the solution with a strong base to a pH of about 10 to about 14, wherein impurities are removed from the Narcotine product.
TOTAL SYNTHESIS OF (+/-)-α-NARCOTINE VIA BISCHLER-NAPIERALSKI CYCLIZATION
Varga, Zsofia,Blasko, Gabor,Doernyei, Gabor,Szantay, Csaba
, p. 831 - 837 (2007/10/02)
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.
Borane Adducts of Narcotine, Hydrastine and Their Reduction Products
Prior, Silvia,Wiegrebe, Wolfgang
, p. 737 - 746 (2007/10/02)
α-Narcotine (3), β-Hydrastine (6) and their reduction products bind BH3 coordinatively at the N atom. α-Narcotinediol (8) when treated with potassium tert.butylate and benzophenone does not yield α-anhydronarcotinediol but leads to a quettamine-like compo
Novel Zinc-Promoted Alkylation of Iminium Salts. New Synthesis of Benzylisoquinoline, Phthalidylisoquinoline, and Protoberberine Alkaloids and Related Compounds
Shono, Tatsuya,Hamaguchi, Hiroshi,Sasaki, Manji,Fujita, Shumei,Nagami, Kimihiko
, p. 1621 - 1628 (2007/10/02)
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.
NEW ELECTROREDUCTIVE SYNTHESIS OF PHTHALIDE ALKALOIDS
Shono, Tatsuya,Usui, Yoshihiro,Hamaguchi, Hiroshi
, p. 1351 - 1354 (2007/10/02)
Electroreduction of 2-methyl-3,4-dihydro-6,7-dimethoxy-isoquinolinium salt in the presence of 3-bromomeconine afforded Cordrastine.The method of cross coupling of immonium salts with bromophthalides was also applicable to other phthalide alkaloids.
