Organocatalytic total synthesis of bioactive compounds based on one-pot methodologies

2021 ◽  
Vol 0 (0) ◽  
Author(s):  
Hélène Pellissier
Keyword(s):  
Total Synthesis ◽  
Bioactive Compounds ◽  
Biologically Active ◽  
Direct Access ◽  
Tandem Reactions ◽  
One Pot ◽  
Total Syntheses ◽  
Asymmetric Organocatalysis ◽  
Key Steps

Abstract The combination of one-pot methodologies to asymmetric organocatalysis allow a green and direct access to many types of complex highly functionalized chiral products, including important key intermediates in total syntheses of important bioactive compounds. A series of chiral organocatalysts have already been successfully applied to such syntheses. This report collects major developments in the total synthesis of biologically active products based on the use of enantioselective organocatalytic domino/tandem reactions as key steps. It is divided into two parts dealing successively with reactions based on the use of proline-derived catalysts and other organocatalysts.

scholarly journals Organocatalytic Asymmetric Tandem/Domino Reactions Towards Access to Bioactive Products

2021 ◽  
Vol 25 ◽  
Author(s):  
Hélène Pellissier
Keyword(s):  
Total Synthesis ◽  
Asymmetric Catalysis ◽  
Biologically Active ◽  
Direct Access ◽  
Tandem Reactions ◽  
Domino Reactions ◽  
Complex Molecules ◽  
Total Syntheses ◽  
Key Steps ◽  
Simple Materials

: Tandem and domino reactions constitute economic routes to complex molecules starting from simple materials. Especially, combining these powerful procedures to asymmetric catalysis allow a direct access to many elaborated chiral products, including important key intermediates in total syntheses of important biologically active compounds. A range of various types of chiral organocatalysts have already been successfully applied to such syntheses. This review presents major developments in the total synthesis of bioactive products based on the use of enantioselective organocatalytic domino/tandem reactions as key steps. It is divided into three parts, dealing successively with syntheses based on organocatalytic asymmetric Michael-initiated domino reactions as key steps; aldol-initiated domino/tandem reactions and other domino reactions.

scholarly journals Total syntheses of all tri-oxygenated 16-phytoprostane classes via a common precursor constructed by oxidative cyclization and alkyl–alkyl coupling reactions as the key steps

2017 ◽  
Vol 15 (44) ◽  
pp. 9408-9414 ◽  
Author(s):  
Jakub Smrček ◽  
Radek Pohl ◽  
Ullrich Jahn
Keyword(s):  
Total Synthesis ◽  
Oxidative Cyclization ◽  
Coupling Reactions ◽  
Total Syntheses ◽  
Common Precursor ◽  
Key Steps

A parallel total synthesis of 16-F1t-, 16-E1-phytoprostanes and a first synthesis of 16-D1t-phytoprostanes based on a common precursor are described.

scholarly journals First Total Synthesis of Artekeiskeanol A, C and Altissimacoumarin D

SynOpen ◽  
2019 ◽  
Vol 03 (02) ◽  
pp. 49-54 ◽  
Author(s):  
Anil Talakokkula ◽  
Karunakar Baikadi ◽  
A. Narsaiah
Keyword(s):  
Total Synthesis ◽  
Oxidation Reactions ◽  
Total Syntheses ◽  
Riley Oxidation ◽  
Key Steps

The total syntheses of artekeiskeanol A and C, and altissimacoumarin D have been achieved. The syntheses commenced from commercially available starting materials, 2,4-dihydroxybenzaldehyde and geraniol. The key steps involve Wittig and Riley oxidation reactions.

Total syntheses of seminolipid and its analogues by using 2,6-bis(trifluoromethyl)phenylboronic acid as protective reagent

2019 ◽  
Vol 17 (31) ◽  
pp. 7325-7329
Author(s):  
Naoyuki Shimada ◽  
Kenji Fukuhara ◽  
Sari Urata ◽  
Kazuishi Makino
Keyword(s):  
Total Synthesis ◽  
Phenylboronic Acid ◽  
Total Syntheses ◽  
Key Steps

Total synthesis of seminolipid was accomplished via regioselective protection using 2,6-bis(trifluoromethyl)phenylboronic acid followed by regioselective trichloroethyl-protected sulfation as key steps.

Asymmetric cyclopropanation of chiral (1-phosphoryl)vinyl sulfoxides: A new approach to constrained analogs of biologically active compounds

2005 ◽  
Vol 77 (12) ◽  
pp. 2091-2098 ◽  
Author(s):  
Marian Mikołajczyk
Keyword(s):  
Transition State ◽  
Total Synthesis ◽  
Bioactive Compounds ◽  
Theoretical Calculations ◽  
Experimental Results ◽  
Biologically Active ◽  
Active Compounds ◽  
New Approach ◽  
Cyclic Analog ◽  
Asymmetric Cyclopropanation

This account outlines the results obtained in the author's laboratory on the asymmetric cyclopropanation of enantiopure 1-phosphorylvinyl p-tolyl sulfoxides with sulfur ylides and diazoalkanes. Based on experimental results and theoretical calculations, the transition-state model for asymmetric cyclopropanation is proposed. A great synthetic value of the reaction investigated is exemplified by the total synthesis of constrained analogs of bioactive compounds, namely, enantiopure cyclic analog of phaclofen and cyclopropylphosphonate analogs of nucleotides.

Asymmetric total synthesis of talienbisflavan A

2018 ◽  
Vol 16 (4) ◽  
pp. 585-592 ◽  
Author(s):  
Deng-Ming Huang ◽  
Hui-Jing Li ◽  
Jun-Hu Wang ◽  
Yan-Chao Wu
Keyword(s):  
Total Synthesis ◽  
Asymmetric Total Synthesis ◽  
Facile Synthesis ◽  
Total Syntheses ◽  
Key Steps

The first asymmetric total syntheses of talienbisflavan A and bis-8,8′-epicatechinylmethane as well as a facile synthesis of bis-8,8′-catechinylmethane has been accomplished from readily available starting materials by using a newly developed direct regioselective methylenation of catechin derivatives as one of the key steps.

Annulations leading to diene systems. Total syntheses of the dolastane-type diterpenoids (±)-(5S,12R,14S)-dolasta-1(15),7,9-trien-14-ol and (±)-amijitrienol

1992 ◽  
Vol 70 (4) ◽  
pp. 1204-1220 ◽  
Author(s):  
Edward Piers ◽  
Richard W. Friesen
Keyword(s):  
Aldol Condensation ◽  
Ring Closure ◽  
Starting Material ◽  
Target Compound ◽  
One Pot ◽  
Stereoselective Reduction ◽  
Total Syntheses ◽  
Reductive Transformation ◽  
The One ◽  
Key Steps

Alkylation of the substituted cycloalkanones 14a–d and 30 with (Z)-1-bromo-4-methyl-3-trimethylstannyl-2-pentene (13) produced compounds 15a–d and 33, which were readily converted into the corresponding enol trifluoromethane-sulfonates (triflates) 16a–d and 34. Intramolecular Pd(O)-catalyzed coupling of the vinylstannane and enol triflate functions in 16a–d and 34 provided the dienes 17a–d and 35. The annulation product 35 served as a suitable starting material for the total syntheses of the dolastane diterpenoids (±)-(5S,12R,14S)-dolasta-1(15),7,9-trien-14-ol (2) and (±)-amijitrienol (3). The key steps of the synthesis of (±)-2 involved the stereoselective methylation of the ketone 44 (readily derived from 35) to provide 46 and the Barbier type ring closure of 47 to provide the target compound. For the synthesis of (±)-3, the notable conversions included the reductive transformation of the diene 35 into the alkene 53, the aldol condensation of the ketone 54 with 4-trimethylstannyl-4-pentenal (55), the chemo- and stereoselective reduction of the dione 58, and the one-pot conversion of the keto vinylstannane 63 into the triene 65, via the intermediate 64.

scholarly journals Total synthesis of ochnaflavone

2013 ◽  
Vol 9 ◽  
pp. 1346-1351 ◽  
Author(s):  
Monica M Ndoile ◽  
Fanie R van Heerden
Keyword(s):  
Total Synthesis ◽  
Oxidative Cyclization ◽  
Experimental Conditions ◽  
Total Syntheses ◽  
Diaryl Ether ◽  
Key Steps

The first total syntheses of ochnaflavone, an asymmetric biflavone consisting of apigenin and luteolin moieties, and the permethyl ether of 2,3,2'',3''-tetrahydroochnaflavone have been achieved. The key steps in the synthesis of ochnaflavone were the formation of a diaryl ether and ring cyclization of an ether-linked dimeric chalcone to assemble the two flavone nuclei. Optimal experimental conditions for the oxidative cyclization to form ochnaflavone were established.

scholarly journals Asymmetric Zinc Catalysis in Green One-Pot Processes

2021 ◽  
Vol 25 ◽  
Author(s):  
Hélène Pellissier
Keyword(s):  
Environmentally Benign ◽  
Direct Access ◽  
Tandem Reactions ◽  
Chiral Molecules ◽  
One Pot ◽  
First Time ◽  
Zinc Catalysis

: This review collects for the first time enantioselective one-pot processes promoted by green chiral zinc catalysts. It illustrates how much these cheap, non-toxic and environmentally benign catalysts allow unprecedented asymmetric domino and tandem reactions of many types to be achieved, allowing a direct access to a wide variety of very complex chiral molecules.

Enantioselective Total Synthesis of Ligraminol D and Ligraminol E

Synlett ◽  
2019 ◽  
Vol 30 (20) ◽  
pp. 2285-2289
Author(s):  
Baliram B. Mane ◽  
D. D. Kumbhar ◽  
Suresh B. Waghmode
Keyword(s):  
Total Synthesis ◽  
Mitsunobu Reaction ◽  
Bioactive Constituents ◽  
Ongoing Research ◽  
Total Syntheses ◽  
Enantioselective Total Synthesis ◽  
Key Steps

As a part of our ongoing research on the synthesis of bioactive constituents or molecules by using an organocatalytic approach, enantioselective total syntheses of ligraminol D and ligraminol E were achieved starting from a commercially available nonchiral aldehyde. Key steps in this synthesis were an asymmetric α-aminoxylation of an aldehyde and a Mitsunobu reaction.

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