An enantioselective total synthesis of Sch-725674

2015 ◽  
Vol 13 (1) ◽  
pp. 234-240 ◽  
Author(s):  
Kota Ramakrishna ◽  
Krishna P. Kaliappan
Keyword(s):  
Total Synthesis ◽  
Metathesis Reaction ◽  
Stereoselective Reduction ◽  
Enantioselective Total Synthesis ◽  
Cross Metathesis ◽  
Yamaguchi Macrolactonization ◽  
Key Steps

An enantioselective total synthesis of Sch-725674 using dithiane alkylation, cross metathesis reaction, Yamaguchi macrolactonization and a substrate controlled stereoselective reduction as key steps is described.

Concise Total Synthesis of Curvulone B

Synlett ◽  
2020 ◽  
Author(s):  
Debendra K. Mohapatra ◽  
Shivalal Banoth ◽  
Utkal Mani Choudhury ◽  
Kanakaraju Marumudi ◽  
Ajit C. Kunwar
Keyword(s):  
Total Synthesis ◽  
Stereoselective Synthesis ◽  
Ring System ◽  
Bond Forming ◽  
Cross Metathesis ◽  
Bond Forming Reactions ◽  
Key Steps

AbstractA concise and convergent stereoselective synthesis of curvulone B is described. The synthesis utilized a tandem isomerization followed by C–O and C–C bond-forming reactions following Mukaiyama-type aldol conditions for the construction of the trans-2,6-disubstituted dihydropyran ring system as the key steps. Other important features of this synthesis are a cross-metathesis, epimerization, and Friedel–Crafts acylation.

First Total Synthesis of a Fluorinated Calystegin

2010 ◽  
Vol 65 (4) ◽  
pp. 445-451 ◽  
Author(s):  
René Csuk ◽  
Erik Prell ◽  
Stefan Reißmann ◽  
Claudia Korb
Keyword(s):  
Total Synthesis ◽  
Ring Opening ◽  
Competitive Inhibitor ◽  
Ring Closure ◽  
Target Compound ◽  
Metathesis Reaction ◽  
Grubbs Catalyst ◽  
Ring Opening Reaction ◽  
Ultrasound Assisted ◽  
Key Steps

A straightforward chiral pool synthesis for the first fluorinated calystegin is described. Key steps of this synthesis include an ultrasound-assisted Zn-mediated tandem ring opening reaction followed by a Grubbs’ catalyst-mediated ring closure metathesis reaction. The target compound is a selective and competitive inhibitor for a β -glycosidase.

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.

scholarly journals Stereoselective Total Synthesis of (6S)-5,6-Dihydro-6-[(2R)-2-hydroxy-6-phenylhexyl]-2H-pyran-2-one from L-Malic Acid

2018 ◽  
Vol 13 (7) ◽  
pp. 1934578X1801300
Author(s):  
Dandekar Chandrakanth ◽  
Yerragorla Gopala Rao ◽  
Tallapally Swamy ◽  
Dhanraj O Biradar ◽  
Lonavath Vishnupriya ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Malic Acid ◽  
Ring Closing Metathesis ◽  
Stereoselective Reduction ◽  
Key Steps ◽  
Barbier Allylation

A stereoselective total synthesis of an antiproliferative and antifungal natural product, (6 S)-5,6-dihydro-6-[(2 R)-2-hydroxy-6-phenylhexyl]-2 H-pyran-2-one has been accomplished using the Barbier allylation, LiAlH4/LiI mediated syn-stereoselective reduction and olefin ring-closing metathesis (RCM) as the key steps. L-Malic acid was used as a chiral precursor for the construction of syn-1,3-diol moiety of the molecule.

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.

scholarly journals Enantioselective Total Synthesis of (–)-Myrifabral A and B

2020 ◽  
Author(s):  
Tyler J. Fulton ◽  
Anthony Chen ◽  
Michael Bartberger ◽  
Brian Stoltz
Keyword(s):  
Total Synthesis ◽  
Allylic Alkylation ◽  
Enantioselective Total Synthesis ◽  
Cross Metathesis ◽  
Quaternary Center ◽  
Tricyclic Core ◽  
Iminium Ion ◽  
Palladium Catalyzed

<p>A catalytic enantioselective approach to the myrioneuron alkaloids (–)-myrifabral A and (–)-myrifabral B is described. The synthesis was enabled by a palladium-catalyzed enantioselective allylic alkylation, that generates the C(10) all-carbon quaternary center. A key N-acyl iminium ion cyclization forged the cyclohexane fused tricyclic core, while vinyl boronate cross metathesis and oxidation afforded the lactol ring of (–)-myrifabral A. Adaptation of previously reported conditions allowed for the conversion of (–)-myrifabral A to (–)-myrifabral B.</p>

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.

Stereoselective Total Synthesis of Arundinolides A and B

Synthesis ◽  
2020 ◽  
Vol 52 (10) ◽  
pp. 1576-1584
Author(s):  
Jun Liu ◽  
Zhi-Bing Dong ◽  
Caizhu Chang ◽  
Jialin Geng ◽  
Yinxin Liu ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Ethyl Lactate ◽  
Metathesis Reaction ◽  
Cross Metathesis ◽  
Key Features ◽  
First Time ◽  
Enantioselective Syntheses

The efficient and enantioselective syntheses of arundinolides A and B have been accomplished for the first time from chiral pool methyl-2,3-O-isopropylidene-β-d-ribofuranoside and d-ethyl lactate. The key features of the total synthesis are intramolecular crotonyl migration and NaBH4-CuCl catalyzed regioselective reduction and cross-metathesis reaction.

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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