scholarly journals Enantioselective synthesis of naturally occurring isoquinoline alkaloids: (S)-(−)-trolline and (R)-(+)-oleracein E

2017 ◽  
Vol 4 (6) ◽  
pp. 958-966 ◽  
Author(s):  
Weilong Lin ◽  
Shengming Ma
Keyword(s):  
Asymmetric Synthesis ◽  
Enantioselective Synthesis ◽  
Isoquinoline Alkaloids ◽  
Highly Efficient ◽  
Naturally Occurring

The highly efficient asymmetric synthesis of a pair of enantiomers, (S)-(−)-trolline and (R)-(+)-oleracein E, has been achieved in five steps.

Enantioselective synthesis of isoquinoline alkaloids: phenylethylisoquinoline and aporphine alkaloids

1987 ◽  
Vol 65 (10) ◽  
pp. 2356-2361 ◽  
Author(s):  
Zbigniew Czarnocki ◽  
David B. MacLean ◽  
Walter A. Szarek
Keyword(s):  
Asymmetric Synthesis ◽  
Tartaric Acid ◽  
Enantiomeric Purity ◽  
Enantioselective Synthesis ◽  
Isoquinoline Alkaloids ◽  
Aporphine Alkaloid ◽  
Ring Systems

A new and improved procedure for the preparation of (R)-2-alkoxycarbonyl-1-formyl-1,2,3,4-tetrahydro-6,7-dimethoxyisoquinolines has been developed beginning from D-(−)-tartaric acid. The utility of these aldehydes in the asymmetric synthesis of isoquinoline alkaloids of high enantiomeric purity has been extended to the synthesis of phenylethylisoquinolines, which have been further transformed in straightforward steps into the homoprotoberberine and homoaporphine ring systems. In this manner, (S)-homolaudanosine, (S)-5′-methoxyhomolaudanosine, (S)-2,3,9,10,11-pentamethoxyhomoprotoberberine, and (S)-O-methylkreysigine have been synthesized. The conversion of (S)-laudanosine to (S)-glaucine, an aporphine alkaloid, has also been realized.

Organocatalytic one-pot asymmetric synthesis of 2-aryl-2,3-dihydro-4-quinolones

RSC Advances ◽  
2016 ◽  
Vol 6 (30) ◽  
pp. 25375-25378 ◽  
Author(s):  
Gao-Fei Pan ◽  
Li Su ◽  
Yan-Lei Zhang ◽  
Shi-Huan Guo ◽  
Yong-Qiang Wang
Keyword(s):  
Asymmetric Synthesis ◽  
Enantioselective Synthesis ◽  
One Pot ◽  
Aryl Aldehydes ◽  
Highly Efficient

A highly efficient organocatalytic one-pot approach for enantioselective synthesis of (R)-2-aryl-2,3-dihydro-4-quinolones from o-aminoacetophenones and aryl aldehydes has been achieved.

Enantioselective synthesis of tetrahydroisoquinolines via catalytic intramolecular asymmetric reductive amination

2021 ◽  
Author(s):  
Ruixia Liu ◽  
Jingkuo Han ◽  
Bin Li ◽  
Xian Liu ◽  
Zhao Wei ◽  
...  
Keyword(s):  
Reductive Amination ◽  
Enantioselective Synthesis ◽  
Iridium Complex ◽  
Highly Efficient ◽  
Efficient Access

A highly efficient intramolecular asymmetric reductive amination transformation catalyzed by an iridium complex of tBu-ax-Josiphos has been realized, providing an efficient access to various THIQ alkaloids.

Enantioselective Functionalization of Prochiral Cyclobutanones and Cyclobutenones

Synlett ◽  
2021 ◽  
Author(s):  
Memg Wang ◽  
Changxu Zhong ◽  
Ping Lu
Keyword(s):  
Asymmetric Synthesis ◽  
Membered Ring ◽  
Enantioselective Synthesis ◽  
Ring Compounds ◽  
Recent Advances ◽  
Cyclobutane Derivatives

Enantioselective synthesis of cyclobutane derivatives is still a challenging topic in asymmetric synthesis. [2+2]-Cycloaddition and skeleton rearrangement are two primary strategies to this end. Recently, functionalization of cyclobutanones and cyclobutenones, which are readily available via [2+2]-cycloadditions as prochiral substrates, has emerged as a powerful tool to access versatile four-membered ring compounds. Herein, we summarize some recent advances in these areas from our and other groups.

Enantioselective synthesis of (+)-goniodiol and of its naturally occurring acetylated analogs

Tetrahedron ◽  
1996 ◽  
Vol 52 (47) ◽  
pp. 14877-14890 ◽  
Author(s):  
Jean-Philippe Surivet ◽  
Jacques Goré ◽  
Jean-Michel Vatèle
Keyword(s):  
Enantioselective Synthesis ◽  
Naturally Occurring

scholarly journals Rhodium-catalyzed asymmetric synthesis of silicon-stereogenic silicon-bridged arylpyridinones

2016 ◽  
Vol 7 (2) ◽  
pp. 1205-1211 ◽  
Author(s):  
Ryo Shintani ◽  
Ryo Takano ◽  
Kyoko Nozaki
Keyword(s):  
Asymmetric Synthesis ◽  
Enantioselective Synthesis ◽  
Catalytic Cycle

A rhodium-catalyzed regio- and enantioselective synthesis of silicon-stereogenic silicon-bridged arylpyridinones was developed. A reasonable catalytic cycle was also experimentally established.

General asymmetric synthesis of isoquinoline alkaloids. Enantioselective hydrogenation of enamides catalyzed by BINAP-ruthenium(II) complexes

1994 ◽  
Vol 59 (2) ◽  
pp. 297-310 ◽  
Author(s):  
Masato Kitamura ◽  
Yi Hsiao ◽  
Masako Ohta ◽  
Masaki Tsukamoto ◽  
Tetsuo Ohta ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Enantioselective Hydrogenation ◽  
Isoquinoline Alkaloids
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