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 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 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 First Stereoselective Total Synthesis of Ciryneol C

SynOpen ◽  
2019 ◽  
Vol 03 (02) ◽  
pp. 59-66
Author(s):  
Ambati Sharada ◽  
Lakshmi Srinivasa Rao Kundeti ◽  
Kallaganti V. S. Ramakrishna ◽  
Kommu Nagaiah
Keyword(s):  
Total Synthesis ◽  
Coupling Reactions ◽  
Asymmetric Total Synthesis ◽  
Acetylene Derivative ◽  
Wittig Olefination ◽  
Epoxide Opening ◽  
Key Steps

The acetylene derivative Ciryneol C was isolated from the roots of C. japonicum. The asymmetric total synthesis of Ciryneol C was achieved in seven steps, with Horner–Wittig olefination, regioselective epoxide opening, and Cadiot–Chodkiewicz coupling reactions being the key steps.

Total syntheses of smenothiazoles A and B

2017 ◽  
Vol 15 (34) ◽  
pp. 7196-7203 ◽  
Author(s):  
Xiao Ma ◽  
Yajie Chen ◽  
Sigui Chen ◽  
Zhengshuang Xu ◽  
Tao Ye
Keyword(s):  
Total Synthesis ◽  
Vinyl Chloride ◽  
Coupling Reactions ◽  
Stille Reaction ◽  
Total Syntheses ◽  
Peptide Coupling ◽  
Diene System

Stereocontrolled installation of vinyl chloride and the 2,5-diene system via silastannation, Stille reaction and desilylchlorination, and the final peptide coupling reactions led to the concise total synthesis of smenothiazoles A (1) and B (2).

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 Ritterazine B

2021 ◽  
Author(s):  
Yasuaki Nakayama ◽  
Michael Maser ◽  
Tatsuya Okita ◽  
Anton V. Dubrovskiy ◽  
Taryn L. Campbell ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Late Stage ◽  
Unified Approach ◽  
Common Precursor ◽  
Key Steps

<a></a>The first total synthesis of the cytotoxic alkaloid ritterazine B is reported. The synthesis features a unified approach to both steroid subunits, employing a titanium-mediated propargylation reaction to achieve divergence from a common precursor. Other key steps include gold-catalyzed cycloisomerizations that install both spiroketals, and late stage C–H oxidation to incorporate the C7<a></a><a>′</a> alcohol.<br>

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 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.

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