scholarly journals A Facile Stereoselective Total Synthesis of (R)-Rugulactone

2014 ◽  
Vol 2014 ◽  
pp. 1-5 ◽  
Author(s):  
B. Narasimha Reddy ◽  
R. P. Singh
Keyword(s):  
Total Synthesis ◽  
Asymmetric Epoxidation ◽  
Cross Metathesis ◽  
Hydride Reduction ◽  
Novel Synthesis ◽  
Metathesis Reactions ◽  
Epoxy Alcohols ◽  
Allyl Alcohols ◽  
Sharpless Asymmetric Epoxidation

An efficient and novel synthesis of (R)-rugulactone has been achieved employing Sharpless asymmetric epoxidation of allyl alcohols followed by selective hydride reduction of epoxy alcohols and olefin cross metathesis reactions.

Enantioselective Synthesis of 4-Amino-3-hydroxybenzopyran Flavanol Derivatives from Chalcones

Synthesis ◽  
2018 ◽  
Vol 50 (24) ◽  
pp. 4796-4808 ◽  
Author(s):  
Leslie Aldrich ◽  
Qiwen Gao ◽  
Lianyan Xu ◽  
Vincent Parise ◽  
Yash Mehta
Keyword(s):  
Biological Evaluation ◽  
Enantioselective Synthesis ◽  
Allylic Alcohol ◽  
Nucleophilic Aromatic Substitution ◽  
Asymmetric Epoxidation ◽  
Aromatic Substitution ◽  
Chemical Library ◽  
Epoxy Alcohols ◽  
Sharpless Asymmetric Epoxidation

A concise method that is easily amenable for analogue synthesis has been developed to enantioselectively access 4-amino-3-hydroxybenzopyrans from chalcones. Epoxy alcohols were formed from chalcones through a Corey–Bakshi–Shibata reduction of the enone and subsequent Sharpless asymmetric epoxidation of the allylic alcohol. The epoxy alcohols were protected, regioselectively opened with various amines using catalytic europium(III) triflate, and the resulting free alcohols were orthogonally protected. Concomitant deprotection and intramolecular nucleophilic aromatic substitution provided the benzopyran core, which is poised to undergo additional reactions to provide a diverse chemical library with ideal properties for biological evaluation.

scholarly journals Applications of Sharpless asymmetric epoxidation in total synthesis

2015 ◽  
Vol 26 (8-9) ◽  
pp. 405-495 ◽  
Author(s):  
Majid M. Heravi ◽  
Tahmineh Baie Lashaki ◽  
Nasim Poorahmad
Keyword(s):  
Total Synthesis ◽  
Asymmetric Epoxidation ◽  
Sharpless Asymmetric Epoxidation

Study of the Cross-Metathesis Reaction of α-Hydroxy β,γ-Unsaturated Amides towards a Rapid and Flexible Total ­Synthesis of Symbioramide and its Isomer

Synlett ◽  
2017 ◽  
Vol 29 (02) ◽  
pp. 230-234 ◽  
Author(s):  
Alexandre Gratais ◽  
Samir Bouzbouz
Keyword(s):  
Methyl Ester ◽  
Total Synthesis ◽  
Metathesis Reaction ◽  
Cross Metathesis ◽  
Metathesis Reactions ◽  
The Cross

The reactivity of novel α-hydroxy β,γ-unsaturated amides in cross-metathesis reactions was extensively studied and used to perform a short total synthesis of symbioramide and its isomer from ­l-serine methyl ester.

ChemInform Abstract: Applications of Sharpless Asymmetric Epoxidation in Total Synthesis

ChemInform ◽  
2015 ◽  
Vol 46 (25) ◽  
pp. no-no
Author(s):  
Majid M. Heravi ◽  
Tahmineh Baie Lashaki ◽  
Nasim Poorahmad
Keyword(s):  
Total Synthesis ◽  
Asymmetric Epoxidation ◽  
Sharpless Asymmetric Epoxidation

scholarly journals Recent Advances in Total Synthesis via Metathesis Reactions

Synthesis ◽  
2018 ◽  
Vol 50 (19) ◽  
pp. 3749-3786 ◽  
Author(s):  
Francisco Sarabia ◽  
Iván Cheng-Sánchez
Keyword(s):  
Total Synthesis ◽  
Tandem Reactions ◽  
Alkyne Metathesis ◽  
Enyne Metathesis ◽  
Metathesis Reaction ◽  
Ring Closing Metathesis ◽  
Total Syntheses ◽  
Cross Metathesis ◽  
Carbon Carbon Bonds ◽  
Metathesis Reactions

The metathesis reactions, in their various versions, have become a powerful and extremely valuable tool for the formation of carbon–carbon bonds in organic synthesis. The plethora of available catalysts to perform these reactions, combined with the various transformations that can be accomplished, have positioned the metathesis processes as one of the most important reactions of this century. In this review, we highlight the most relevant synthetic contributions published between 2012 and early 2018 in the field of total synthesis, reflecting the state of the art of this chemistry and demonstrating the significant synthetic potential of these methodologies.1 Introduction2 Alkene Metathesis in Total Synthesis2.1 Total Synthesis Based on a Ring-Closing-Metathesis Reaction2.2 Total Synthesis Based on a Cross-Metathesis Reaction2.3 Strategies for Selective and Efficient Metathesis Reactions of Alkenes2.3.1 Temporary Tethered Ring-Closing Metathesis2.3.2 Relay Ring-Closing Metathesis2.3.3 Stereoselective Alkene Metathesis2.3.4 Alkene Metathesis in Tandem Reactions3 Enyne Metathesis in Total Synthesis3.1 Total Syntheses Based on a Ring-Closing Enyne-Metathesis Reaction3.2 Total Syntheses Based on an Enyne Cross-Metathesis Reaction3.3 Enyne Metathesis in Tandem Reactions4 Alkyne Metathesis in Total Synthesis4.1 Total Synthesis Based on a Ring-Closing Alkyne-Metathesis Reaction4.2 Other Types of Alkyne-Metathesis Reactions5 Conclusions

scholarly journals A protecting group-free synthesis of the Colorado potato beetle pheromone

2013 ◽  
Vol 9 ◽  
pp. 2374-2377 ◽  
Author(s):  
Zhongtao Wu ◽  
Manuel Jäger ◽  
Jeffrey Buter ◽  
Adriaan J Minnaard
Keyword(s):  
Aggregation Pheromone ◽  
Colorado Potato Beetle ◽  
Leptinotarsa Decemlineata ◽  
Alcohol Oxidation ◽  
Asymmetric Epoxidation ◽  
Protecting Group ◽  
Novel Synthesis ◽  
Potato Beetle ◽  
Sharpless Asymmetric Epoxidation

A novel synthesis of the aggregation pheromone of the Colorado potato beetle, Leptinotarsa decemlineata, has been developed based on a Sharpless asymmetric epoxidation in combination with a chemoselective alcohol oxidation using catalytic [(neocuproine)PdOAc]2OTf2. Employing this approach, the pheromone was synthesized in 3 steps, 80% yield and 86% ee from geraniol.

First Total Synthesis of Jomthonic Acid A

Synlett ◽  
2019 ◽  
Vol 31 (01) ◽  
pp. 69-72
Author(s):  
Mohan Dumpala ◽  
Batthula Srinivas ◽  
Palakodety Radha Krishna
Keyword(s):  
Amino Acid ◽  
Total Synthesis ◽  
Mitsunobu Reaction ◽  
Asymmetric Epoxidation ◽  
Synthetic Strategy ◽  
Amide Coupling ◽  
Key Features ◽  
Sharpless Asymmetric Epoxidation

A stereoselective total synthesis of jomthonic acid A is described. The key features of the synthetic strategy are a Sharpless asymmetric epoxidation, a Gilmann reagent-induced methylation, a Mitsunobu reaction, a Yamaguchi esterification, and an O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (TBTU)-mediated amide coupling. Jomthonic acid A is an architecturally rare amino acid containing a β-methylphenylalanine residue and a 4-methyl-(2E,4E)-hexa-2,4-dienoate moiety. It shows antidiabetic and antiatherogenic activities when tested against mouse ST-13 preadiopocytes.

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