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.

scholarly journals Enantiomeric Tartaric Acid Production Using cis-Epoxysuccinate Hydrolase: History and Perspectives

Molecules ◽  
2019 ◽  
Vol 24 (5) ◽  
pp. 903 ◽  
Author(s):  
Jinsong Xuan ◽  
Yingang Feng
Keyword(s):  
Tartaric Acid ◽  
Acid Production ◽  
Enantiomeric Excess ◽  
Enantiomeric Purity ◽  
Enantioselective Synthesis ◽  
Future Research ◽  
Tartaric Acids ◽  
Catalytic Mechanisms ◽  
Very High ◽  
Hydrophilic Molecule

Tartaric acid is an important chiral chemical building block with broad industrial and scientific applications. The enantioselective synthesis of l(+)- and d(−)-tartaric acids has been successfully achieved using bacteria presenting cis-epoxysuccinate hydrolase (CESH) activity, while the catalytic mechanisms of CESHs were not elucidated clearly until very recently. As biocatalysts, CESHs are unique epoxide hydrolases because their substrate is a small, mirror-symmetric, highly hydrophilic molecule, and their products show very high enantiomeric purity with nearly 100% enantiomeric excess. In this paper, we review over forty years of the history, process and mechanism studies of CESHs as well as our perspective on the future research and applications of CESH in enantiomeric tartaric acid production.

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.

A Short Enantioselective Synthesis of (S)-Levetiracetam Through Direct Pd-Catalyzed Asymmetric N-Allylation of Methyl 4-Aminobutyrate

Synlett ◽  
2021 ◽  
Author(s):  
Dominik Albat ◽  
Jörg-Martin Neudörfl ◽  
Hans-Günther Schmalz
Keyword(s):  
Antiepileptic Drug ◽  
Tartaric Acid ◽  
Enantioselective Synthesis

An exceedingly short and enantioselective synthesis of the antiepileptic drug (S)-levetiracetam was elaborated. As the chirogenic key step a Pd-catalyzed asymmetric N-allylation of methyl 4-aminobutyrate was achieved in the presence of only 1 mol% of a catalyst prepared in situ from [Pd(allyl)Cl]2 and the tartaric acid-derived C2-symmetric diphosphane ligand (S,S)-iPr-MediPhos).

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.

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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