47355-66-8Relevant articles and documents
Total Synthesis of (-)-Canadine, (-)-Rotundine, (-)-Sinactine, and (-)-Xylopinine Using a Last-Step Enantioselective Ir-Catalyzed Hydrogenation
Chen, Fener,Chen, Wenchang,Chen, Yu,Jiang, Meifen,Li, Weijian,Tang, Pei,Yang, Zhi
, p. 8143 - 8153 (2021/06/28)
A concise asymmetric total synthesis of a group of tetrahydroprotoberberine alkaloids, (-)-canadine, (-)-rotundine, (-)-sinactine, and (-)-xylopinine, has been accomplished in three steps from the commercially available corresponding disubstituted phenylethylamine and disubstituted benzaldehyde. Our synthesis toward these four alkaloids took advantage of the following strategy: In the first step, we achieved an efficient and sustainable synthesis of secondary amine hydrochlorides via a fully continuous flow; in the second step, we developed a Pictet-Spengler reaction/Friedel-Crafts hydroxyalkylation/dehydration cascade for the construction of the dihydroprotoberberine core structure (ABCD-ring); and in the last step, Ir-catalyzed enantioselective hydrogenation was employed for the introduction of the desired stereochemistry at the C-14 position in the tetrahydroprotoberberine alkaloids. This work significantly expedites the asymmetric synthesis of the entire tetrahydroprotoberberine alkaloid family as well as a more diverse set of structurally related non-natural analogues.
Synthesis and antihyperglycemic evaluation of various protoberberine derivatives
Bian, Xiaoli,He, Langchong,Yang, Guangde
, p. 1380 - 1383 (2007/10/03)
Various berberine derivatives (2-17) were synthesized and their antihyperglycemic activities were evaluated in a model of β-cell-membrane chromatography and a model of alloxan-induced diabetes mice. The results indicated that compounds 5 and 14 exhibited antihyperglycemic activity. Their structure-activity relationships were discussed.
Chiral acetylenic sulfoxides in organic synthesis: Secondary amine cyclization and total synthesis of (S)-(-)-carnegine
Chan, Winghong,Lee, Albert W. M.,Jiang, Lasheng
, p. 715 - 718 (2007/10/02)
Michael addition of secondary amines 1b-1g onto chiral acetylenic sulfoxides 2 followed by acid induced cyclization afforded structures of tetrahydroisoquinoline skeleton in high to moderate diastereoselectivity. Optical pure (S)-(-)-carnegine has been sy