91940-89-5Relevant academic research and scientific papers
Synthesis and crystal structure of (4s)-4-benzyl-3-(4,5-dimethoxy-2-methylbenzoyl)- 2,2-dimethyl-1,3-oxazolidine
Chrzanowskak, Maria,Meissner, Zofia,Chrzanowska, Joanna M.,Gzella, Andrzej K.
, p. 730 - 739 (2015/03/04)
The synthesis of (4S)-4-benzyl-3-(4,5-dimethoxy-2-methylbenzoyl)- 2,2-dimethyl-1,3-oxazolidine 6 was performed in 7 steps starting from veratraldehyde 7. A new oxidizing system TBHP-ebselen 12 was used for oxidation of 4,5-dimethoxy-2-methylbenzaldehyde 11 into carboxylic acid 13, being the crucial step of the synthesis. The latter was transformed first to chiral amide 14 using (S)-phenylalaninol and then cyclised to oxazolidine 6. The spatial structure and the absolute configuration of the latter one was confirmed by X-ray study.
Enantiospecific synthesis of (S)-(-)-8-oxoxylopinine
Meissner, Zofia,Chrzanowska, Maria
, p. 225 - 229 (2015/03/04)
The enantiospecific synthesis of (S)-(-)-8-oxoxylopinine 1 was performed using a lateral metallation strategy, in which (S)-alaninol or (S)-phenylalaninol was applied as chiral auxiliary and building block. (4S)-3-(4,5-Dimethoxy-2-methylbenzoyl)-2,2,4-tri
First total synthesis of the phenolic 7,8-dihydro-8-oxoprotoberberine alkaloid, cerasonine
Le, Thanh Nguyen,Cho, Won-Jea
experimental part, p. 1026 - 1029 (2009/07/18)
First total synthesis of the phenolic protoberberine, cerasonine, was accomplished through a coupling reaction between o-toluamide and benzonitrile. This key step provided the 3-arylisoquinoline which was then successfully converted to 7,8-dihydro-8-oxoprotoberberine through an intramolecular S N2 reaction.
Synthesis of both enantiomers of protoberberines via laterally lithiated (S)-4-isopropyl-2-(o-tolyl)-oxazolines
Fukuda, Tsutomu,Iwao, Masatomo
, p. 701 - 720 (2008/09/18)
The addition of the laterally lithiated (S)-4-isopropyl-2-(o- tolyl)oxazoline (1) to 6,7-dimethoxy-3,4-dihydroisoquinoline (2) proceeded in modest diastereoselectivity. However, the addition products (3a) and (3b) were easily separated by column chromatography over silica gel. Acid-catalyzed lactamization of 3a and 3b followed by LiAlH4-reduction afforded the corresponding optically pure protoberberines (8a) and (8b), respectively. This procedure was successfully applied to the synthesis of both enantiomers of xylopinine and bharatamine.
A Versatile Total Synthesis of Benzo[c]phenanthridine and Protoberberine Alkaloids Using Lithiated Toluamide-Benzonitrile Cycloaddition
Le, Thanh Nguyen,Gang, Seong Gyoung,Cho, Won-Jea
, p. 2768 - 2772 (2007/10/03)
A new versatile synthesis of benzo[c]phenanthridine and protoberberine alkaloids using lithiated toluamide-benzonitrile cycloaddition was carried out. The coupling reaction between benzonitrile 6 with o-toluamides (8a-c) afforded 3-arylisoquinolines (9a-c
