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.

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 Relay cross metathesis reactions of vinylphosphonates

2014 ◽  
Vol 10 ◽  
pp. 1933-1941 ◽  
Author(s):  
Raj K Malla ◽  
Jeremy N Ridenour ◽  
Christopher D Spilling
Keyword(s):  
Reaction Mechanism ◽  
Metathesis Reaction ◽  
Grubbs Catalyst ◽  
Cross Metathesis ◽  
Metathesis Reactions ◽  
Terminal Alkenes ◽  
The Cross

Dimethyl (β-substituted) vinylphosphonates do not readily undergo cross metathesis reactions with Grubbs catalyst and terminal alkenes. However, the corresponding mono- or diallyl vinylphosphonate esters undergo facile cross metathesis reactions. The improved reactivity is attributed to a relay step in the cross metathesis reaction mechanism.

Complete Stereocontrol in the Synthesis of Harmonine and Novel Analogues Facilitated by a Grubbs Z-Selective Cross-Metathesis Catalyst

2015 ◽  
Vol 68 (12) ◽  
pp. 1815 ◽  
Author(s):  
Steven-Alan G. Abel ◽  
Wesley J. Olivier ◽  
Richard L. Pederson ◽  
Alex C. Bissember ◽  
Jason A. Smith
Keyword(s):  
The Self ◽  
Metathesis Reaction ◽  
Cross Metathesis ◽  
Metathesis Catalyst ◽  
The Cross

(R)-Harmonine was synthesised in 15 % overall yield via a six-step sequence exploiting a Z-selective cross-metathesis reaction as its centrepiece. By this strategy, the cis-olefin present in the target could be installed exclusively. The use of an alcohol and an ester as the amine precursors was crucial for isolating the cross-metathesis product from the self-metathesis products. This method was also used to prepare two novel analogues of harmonine.

Regulation of the degree of blockiness of the norbornene–cyclooctene copolymer synthesized via the cross-metathesis reaction

2016 ◽  
Vol 58 (3) ◽  
pp. 292-297 ◽  
Author(s):  
Yu. I. Denisova ◽  
M. L. Gringolts ◽  
L. B. Krentsel’ ◽  
G. A. Shandryuk ◽  
A. D. Litmanovich ◽  
...  
Keyword(s):  
Metathesis Reaction ◽  
Cross Metathesis ◽  
The Cross

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.

scholarly journals Cross-metathesis reaction of α- and β-vinyl C-glycosides with alkenes

2015 ◽  
Vol 11 ◽  
pp. 1392-1397 ◽  
Author(s):  
Ivan Šnajdr ◽  
Kamil Parkan ◽  
Filip Hessler ◽  
Martin Kotora
Keyword(s):  
Metathesis Reaction ◽  
Simple Method ◽  
Cross Metathesis ◽  
Terminal Alkenes ◽  
The Cross

Cross-metathesis of α- and β-vinyl C-deoxyribosides and α-vinyl C-galactoside with various terminal alkenes under different conditions was studied. The cross-metathesis of the former proceeded with good yields of the corresponding products in ClCH2CH2Cl the latter required the presence of CuI in CH2Cl2 to achieve good yields of the products. A simple method for the preparation of α- and β-vinyl C-deoxyribosides was also developed. In addition, feasibility of deprotection and further transformations were briefly explored.

Ruthenium-catalyzed cross-metathesis with electron-rich phenyl vinyl sulfide enables access to 2,3-dideoxy-d-ribopyranose ring system donors

RSC Advances ◽  
2014 ◽  
Vol 4 (38) ◽  
pp. 19794-19799 ◽  
Author(s):  
Omar Boutureira ◽  
M. Isabel Matheu ◽  
Yolanda Díaz ◽  
Sergio Castillón
Keyword(s):  
Microwave Irradiation ◽  
Ring System ◽  
Metathesis Reaction ◽  
Vinyl Sulfide ◽  
Cross Metathesis ◽  
The Cross ◽  
Flexible Metal ◽  
Phenyl Vinyl

Microwave irradiation effectively accelerates the cross-metathesis reaction of 2-deoxy-d-ribose hydroxyalkene and derivatives with electron-rich phenyl vinyl sulfide using commercially available ruthenium-based catalysts, thus providing a flexible metal-mediated route to 2,3-dideoxy-d-ribopyranose ring system donors.

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.

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