scholarly journals Stereoselective Total Synthesis of 1,4-Dideoxy-1,4-imino-L-ribitol by an Intramolecular Ring Opening of Epoxide with a Tethered Amide

2018 ◽  
Vol 13 (8) ◽  
pp. 1934578X1801300 ◽  
Author(s):  
Chaya N Dhudmal ◽  
Dhanraj O Biradar ◽  
Maddipatla V. Satyanarayana ◽  
Basi V Subba Reddy
Keyword(s):  
Total Synthesis ◽  
Ring Opening ◽  
Amido Group ◽  
Ring Opening Of Epoxide ◽  
Intramolecular Ring

Stereoselective total synthesis of 1,4-dideoxy-1,4-imino-L-ribitol has been accomplished from D-glucose. The key step involved in this synthesis is the regioselective ring-opening of the epoxide with a tethered amido group to give the N-tosyl-3,6-dideoxy-3,6-imino-1,2- O-isopropylidene-α-D-glucofuranose.

scholarly journals A Unified Total Synthesis of Isocyclocapitelline and Cyclocapitelline

2020 ◽  
Vol 15 (11) ◽  
pp. 1934578X2096787
Author(s):  
Marepally Srilatha ◽  
Vallabhareddy Satteyyanaidu ◽  
Chepyala Krishna Reddy ◽  
Venkata Subba Reddy Basireddy
Keyword(s):  
Total Synthesis ◽  
Ring Opening ◽  
Ring Opening Of Epoxide ◽  
Key Steps ◽  
Neutral Conditions ◽  
Intramolecular Ring

A facile and concise synthesis of β-carboline alkaloids, such as (–)-isocyclocapitelline and (+)-cyclocapitelline, has been achieved from commercially available geraniol through a unified strategy. The key steps involved in this synthesis are Sharpless epoxidation, intramolecular ring opening of epoxide, Pictet-Spengler reaction, and dehydrogenative aromatization using 10% palladium/carbon in xylene under neutral conditions.

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.

Intramolecular Ring-Opening Decomposition of Aryl Azetidines

2021 ◽  
Vol 12 (10) ◽  
pp. 1585-1588
Author(s):  
Guoyun Bai ◽  
Thomas N. O’Connell ◽  
Michael A. Brodney ◽  
Christopher R. Butler ◽  
Lara C. Czabaniuk ◽  
...  
Keyword(s):  
Ring Opening ◽  
Intramolecular Ring

Total Synthesis of Resolvin T4

Synlett ◽  
2021 ◽  
Author(s):  
Narihito Ogawa ◽  
Kohei Arai ◽  
Yuichi Kobayashi
Keyword(s):  
Total Synthesis ◽  
Ring Opening ◽  
Transfer Hydrogenation ◽  
Asymmetric Transfer Hydrogenation ◽  
Ring Opening Reaction ◽  
Propargylic Alcohol ◽  
Chiral Centers ◽  
Wittig Reactions

AbstractA total synthesis of resolvin T4 was achieved by connecting three intermediates by Wittig reactions. The enal in the C1–C10 part was constructed through reduction of a propargylic alcohol with Red-Al followed by oxidation. The enal moiety in the C11–C16 part was synthesized by a ring-opening reaction of a silyl epoxide followed by a Peterson elimination. The chiral centers at C7 and C13 were constructed by ruthenium-catalyzed asymmetric transfer hydrogenation.

Structural Investigation of a Configurationally Stable Seven-Membered Bridged Biaryl of Relevance for Atroposelective Biaryl Syntheses*

2003 ◽  
Vol 58 (2-3) ◽  
pp. 231-236 ◽  
Author(s):  
Gerhard Bringmann ◽  
Robert-Michael Pfeifer ◽  
Christian Rummey ◽  
Thomas Pabst ◽  
Dirk Leusser ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Ring Opening ◽  
Structural Investigation ◽  
X Ray Diffraction ◽  
Cleavage Reaction ◽  
Perfect Agreement ◽  
X Ray ◽  
Ether Bridge ◽  
Axially Chiral ◽  
Aromatic Systems

The atroposelective ring opening of lactone-bridged biaryl systems is the key step in the total synthesis of a series of axially chiral biaryl natural products and useful reagents or catalysts for asymmetric synthesis. For a more in-depth understanding of the mechanism and stereochemical course of this remarkable cleavage reaction, a seven-membered ether analog of such useful biaryl lactones has been investigated structurally, both experimentally, by X-ray diffraction analysis, and by ab initio calculations (B3LYP/6-31G*). In a nearly perfect agreement, both methods show that these seven-membered bridged biaryls do not constitute helicene-like distorted molecules, but ‘true’ biaryls, whose sufficiently long lactone or ether bridge allows the two aromatic systems to adopt a large dihedral angle to each other, without any noticeable deviation from planarity for the two aromatic systems - in contrast to related six-membered analogs, which can rather be considered as helicene-like twisted polycyclic systems.

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