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.

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 Bioinspired Oxidative Cyclization of the Geissoschizine Skeleton for the Enantioselective Total Synthesis of Mavacuran Alkaloids

2019 ◽  
Author(s):  
Maxime Jarret ◽  
Victor Turpin ◽  
Aurélien Tap ◽  
Jean-Francois Gallard ◽  
Cyrille Kouklovsky ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Oxidative Coupling ◽  
Indole Alkaloids ◽  
Oxidative Cyclization ◽  
Total Syntheses ◽  
Enantioselective Total Synthesis ◽  
Biosynthetic Precursor ◽  
Monoterpene Indole Alkaloids ◽  
Coupling Approach

We report the enantioselective total syntheses of mavacurans alkaloids, (+)-taberdivarine H, (+)-16-hydoxymethyl-pleiocarpamine, (+)-16-epi-pleiocarpamine, and their postulated biosynthetic precursor 16-formyl-pleiocarpamine. This family of monoterpene indole alkaloids is a target of choice since some of its members are subunits of intricate bisindole alkaloids such as bipleiophylline. Inspired by the biosynthetic hypothesis, we explored an oxidative coupling approach from the geissoschizine framework to form the N1-C16 bond. Quaternization of the aliphatic nitrogen was key to achieve the oxidative coupling induced by KHMDS/I<sub>2 </sub>since<sub> </sub>it hides the nucleophilicity of the aliphatic nitrogen and locks the required cis conformation.

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.

scholarly journals Enantioselective total synthesis of decytospolide A and decytospolide B using an Achmatowicz reaction

2018 ◽  
Vol 16 (33) ◽  
pp. 5979-5986 ◽  
Author(s):  
Arun K. Ghosh ◽  
Hannah M. Simpson ◽  
Anne M. Veitschegger
Keyword(s):  
Total Synthesis ◽  
Transfer Hydrogenation ◽  
Enantioselective Total Synthesis ◽  
Key Steps ◽  
Enantioselective Syntheses

Enantioselective syntheses of decytospolides are described using an Achmatowicz rearrangement, transfer hydrogenation and Friedel–Crafts acylation as the key steps.

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.

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.

Enantioselective total synthesis of (S)-nakinadine B

RSC Advances ◽  
2016 ◽  
Vol 6 (31) ◽  
pp. 25913-25917 ◽  
Author(s):  
Yuvraj Garg ◽  
Satyendra Kumar Pandey
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Michael Addition ◽  
Marine Natural Product ◽  
Enantioselective Total Synthesis ◽  
Novel Approach ◽  
Key Steps

A novel approach for the synthesis of (S)-nakinadine B, a marine natural product is described. The synthesis utilizes the optimized combination of organocatalyzed Michael addition and aminoxylation reactions as key steps.

Total Synthesis of (–)-Aristoquinoline via an Intramolecular Nitrilium Ion Cyclization

Synthesis ◽  
2021 ◽  
Author(s):  
Keith P. Reber ◽  
Priyansh D. Gujarati
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Building Block ◽  
Spectroscopic Properties ◽  
Ring System ◽  
Synthetic Route ◽  
Enantioselective Total Synthesis ◽  
Key Steps

AbstractThe enantioselective total synthesis of the alkaloid aristoquinoline has been achieved in seven steps and 26% overall yield. A new preparation of the useful synthetic building block (–)-α-terpinyl amine was also developed in order to avoid stoichiometric mercury reagents or azide-containing intermediates. Key steps in the optimized synthetic route include an intramolecular nitrilium ion cyclization to form the characteristic azabicyclo[3.3.1]nonane ring system and a dia­stereoselective reduction of the resulting imine mixture to afford the natural product. An isomer of aristoquinoline containing an exocyclic alkene was also obtained and found to exhibit unusual chromatographic and spectroscopic properties.

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