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.

Total synthesis of haliclamide

2016 ◽  
Vol 14 (39) ◽  
pp. 9287-9293 ◽  
Author(s):  
Suraksha Gahalawat ◽  
Satyendra Kumar Pandey
Keyword(s):  
Total Synthesis ◽  
Stereoselective Synthesis ◽  
Steglich Esterification ◽  
Key Steps

A stereoselective synthesis of haliclamide has been developed. The synthesis includes MacMillan cross aldol, Mitsunobu inversion, Yamaguchi–Hirao alkylation, Steglich esterification and macrolactamization reactions and the Corey–Fuchs protocol as the key steps.

scholarly journals Synthesis of the Trans-Syn-Trans Perhydrobenzo[f]chromene Ring System

2021 ◽  
Author(s):  
Amjad Ayad Qatran AlKhdhairawi ◽  
Syahrul Imran ◽  
Nurhuda Manshoor ◽  
Geoffrey A. Cordell ◽  
Narendra Babu Shivanagere Nagojappa ◽  
...  
Keyword(s):  
Stereoselective Synthesis ◽  
Ring System ◽  
Unsaturated Ketone ◽  
Target Compound ◽  
Reductive Alkylation ◽  
Acid Catalyzed ◽  
Key Steps ◽  
Chromene Ring

<p>A stereoselective synthesis of the <i>trans</i>-<i>syn</i>-<i>trans </i>perhydrobenzo[<i>f</i>]chromene skeleton is presented. The target compound <b>3 </b>was achieved in six steps starting from the (<i>S</i>)-(+)-Wieland-Miescher ketone. Key steps include the sp<sup>2</sup> alkylation at the a-carbon of an unsaturated ketone, Birch-type reductive alkylation, and an acid-catalyzed cyclization. </p>

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.

Chiron approach for the total synthesis of brevipolide M

Synlett ◽  
2022 ◽  
Author(s):  
Yang Liu ◽  
Ziyang Zhao ◽  
Chao Hu ◽  
Chuanfang Zhao ◽  
Jun Liu ◽  
...  
Keyword(s):  
Double Bond ◽  
Total Synthesis ◽  
Stereoselective Synthesis ◽  
Ring Closing Metathesis ◽  
One Pot ◽  
Double Bond Migration ◽  
Key Steps

An efficient stereoselective synthesis of brevipolide M was established in 13 linear steps and 17.8% overall yields base on chiron approach. The key steps of our synthesis involved tandem homologation / tetrahydrofuran cyclization and sequential ring-closing metathesis (RCM) / double-bond migration in one-pot processes.

scholarly journals Application of cyclic phosphonamide reagents in the total synthesis of natural products and biologically active molecules

2014 ◽  
Vol 10 ◽  
pp. 1848-1877 ◽  
Author(s):  
Thilo Focken ◽  
Stephen Hanessian
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Bioactive Compounds ◽  
Biologically Active ◽  
Bond Forming ◽  
Michael Additions ◽  
Bond Forming Reactions ◽  
Asymmetric Alkylations

A review of the synthesis of natural products and bioactive compounds adopting phosphonamide anion technology is presented highlighting the utility of phosphonamide reagents in stereocontrolled bond-forming reactions. Methodologies utilizing phosphonamide anions in asymmetric alkylations, Michael additions, olefinations, and cyclopropanations will be summarized, as well as an overview of the synthesis of the employed phosphonamide reagents.

A Facile Total Synthesis of Mubritinib

Synthesis ◽  
2021 ◽  
Vol 53 (05) ◽  
pp. 978-982
Author(s):  
Chunxiang Kuang ◽  
Rong Wang ◽  
Menghan Cui ◽  
Qing Yang
Keyword(s):  
Total Synthesis ◽  
Click Reaction ◽  
Triazole Ring ◽  
Ring System ◽  
Industrial Scale ◽  
Key Steps ◽  
The Way

AbstractA five-step, practical, and concise total synthesis of mubritinib is described. The synthesis utilized Friedel–Crafts acylation, click reaction, reduction, and demethylation for the construction of the triazole ring system as key steps. Another important feature of this synthesis is the Bredereck oxazole synthesis. The main advantages of this process are the improved yield and decreased number of reaction steps, which paves the way for the industrial-scale synthesis of mubritinib.

Enolizable Alkylidene Heterocyclic and Carbocyclic Carbonyl Systems­: Valuable Vinylogous Donor Substrates in Synthesis

Synthesis ◽  
2017 ◽  
Vol 49 (11) ◽  
pp. 2297-2336 ◽  
Author(s):  
Lucia Battistini ◽  
Claudio Curti ◽  
Gloria Rassu ◽  
Andrea Sartori ◽  
Franca Zanardi
Keyword(s):  
Carbonyl Compounds ◽  
Stereoselective Synthesis ◽  
Chemical Transformations ◽  
Carbon Bond ◽  
Bond Forming ◽  
Carbon Carbon Bond ◽  
Bond Forming Reactions

Controlled vinylogous carbon–carbon bond-forming reactions are useful options for providing the selective remote functionalization of conjugated carbonyl substrates. Remotely enolizable alkylidene heterocyclic and carbocyclic carbonyl compounds are pro-nucleophilic substrates that may be engaged in highly valuable chemical transformations. This review emphasizes the merits of these recently discovered vinylogous donors in the chemo-, regio- and stereoselective synthesis of many functionality-rich products.1 Introduction2 Alkylidene Oxindoles3 Alkylidene Pyrazolinones4 Alkylidene Furanones5 Alkylidene Azlactones6 Cycloalkylidene Carbonyl Compounds7 Alkylidene Indenones8 Cycloalkylidene Malononitriles9 Conclusion

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.

scholarly journals Conjugated nitrosoalkenes as Michael acceptors in carbon–carbon bond forming reactions: a review and perspective

2017 ◽  
Vol 13 ◽  
pp. 2214-2234 ◽  
Author(s):  
Yaroslav Dmitrievich Boyko ◽  
Valentin Sergeevich Dorokhov ◽  
Alexey Yu Sukhorukov ◽  
Sema Leibovich Ioffe
Keyword(s):  
Total Synthesis ◽  
Organic Synthesis ◽  
Michael Addition ◽  
High Reactivity ◽  
Carbon Bond ◽  
Bond Forming ◽  
Carbon Carbon Bond ◽  
Bond Forming Reactions ◽  
Recent Developments ◽  
Michael Acceptors

Despite of their chemical instability and high reactivity, conjugated nitrosoalkenes are useful intermediates in target-oriented organic synthesis. The present review deals with carbon–carbon bond forming reactions involving Michael addition to α-nitrosoalkenes with a particular focus on recent developments in this methodology and its use in total synthesis.

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