A Convergent Total Synthesis of Ustiloxin D via an Unprecedented Copper-Catalyzed Ethynyl Aziridine Ring-Opening by Phenol Derivatives

2005 ◽  
Vol 7 (23) ◽  
pp. 5325-5327 ◽  
Author(s):  
Pixu Li ◽  
Cory D. Evans ◽  
Madeleine M. Joullié
Keyword(s):  
Total Synthesis ◽  
Ring Opening ◽  
Aziridine Ring ◽  
Phenol Derivatives ◽  
Ustiloxin D ◽  
Ethynyl Aziridine

scholarly journals Intramolecular N–Me and N–H aminoetherification for the synthesis of N-unprotected 3-amino-O-heterocycles

2021 ◽  
Author(s):  
Mahesh P. Paudyal ◽  
Mingliang Wang ◽  
Juha H. Siitonen ◽  
Yimin Hu ◽  
Muhammed Yousufuddin ◽  
...  
Keyword(s):  
Ring Opening ◽  
Domino Reaction ◽  
Aziridine Ring

A mild Rh-catalyzed method for synthesis of cyclic unprotected N–Me and N–H 2,3-aminoethers using an olefin aziridination–aziridine ring-opening domino reaction has been developed.

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.

Stereoselective Syntheses of 4-Oxa Diaminopimelic Acid and Its Protected Derivatives via Aziridine Ring Opening

2007 ◽  
Vol 9 (21) ◽  
pp. 4211-4214 ◽  
Author(s):  
Hongqiang Liu ◽  
Vijaya R. Pattabiraman ◽  
John C. Vederas
Keyword(s):  
Ring Opening ◽  
Diaminopimelic Acid ◽  
Aziridine Ring ◽  
Stereoselective Syntheses

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.

Total Synthesis of Monosaccharides. Synthesis of Methyl DL-Pentopyranosides with α- and β-lyxo, β-ribo, α-xylo, and α-arabino Configurations from Furfuryl Alcohol

1975 ◽  
Vol 53 (17) ◽  
pp. 2524-2529 ◽  
Author(s):  
Osman Achmatowicz Jr. ◽  
Pawel Bukowski
Keyword(s):  
Total Synthesis ◽  
Ring Opening ◽  
Furfuryl Alcohol ◽  
Oxirane Ring

Hydroxylation and epoxidation, followed by the oxirane ring opening, of methyl 2,3-dideoxy-α and β-DL-pent-2-enopyranosides, readily available by the transformation of furfuryl alcohol, afforded the title compounds. Steric course of hydroxylation and epoxidation reactions were examined. The p.m.r. data of methyl 4-O-acetyl-2,3-anhydro-DL-pentopyranosides are reported.

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