Synthesis of Methyl 1, 5‐Diaryl‐1H ‐pyrrole‐2‐carboxylates via Acid‐catalyzed Ring‐opening/Ring‐closure Sequence

2021 ◽  
Author(s):  
Long Huang ◽  
Chenghao Luo ◽  
Pan Pan Xu ◽  
Bing Liu ◽  
Duntie Zhang ◽  
...  
Keyword(s):  
Ring Opening ◽  
Ring Closure ◽  
Acid Catalyzed

The chemistry of thujone. XVII. The synthesis of ambergris fragrances and related analogues

1994 ◽  
Vol 72 (6) ◽  
pp. 1570-1581 ◽  
Author(s):  
James P. Kutney ◽  
Yong-Huang Chen
Keyword(s):  
Ring Opening ◽  
Sodium Acetate ◽  
Ring Closure ◽  
Side Chain ◽  
Synthetic Route ◽  
Acid Catalyzed ◽  
Robinson Annulation

A strategy to utilize the thujone-derived enone 1 for the development of a synthetic route to ambergris fragrances is presented. Thujone (8) is transformed to the tricyclic enone 9, via the Robinson annulation reaction, and the latter is then elaborated to the cis-fused tricyclic intermediates 10, 11, and 12. Extrusion of the isopropyl side chain in 12 is achieved through an initial ozonation reaction and the resulting ketone 14 is then treated with m-CPBA to afford 16. Cyclopropyl ring opening in 16 is performed via initial saponification to the alcohol 17 and the latter is then reacted with FeCl3 and sodium acetate to enone 1. The necessary elaboration of a tetrahydrofuran ring attached to ring B of 1 is achieved through reaction of 1 with vinylmagnesium bromide, alkylation, hydroboration, and final acid-catalyzed ring closure of the 1,5-diol 4. The route affords the opportunity of synthesizing a variety of analogues within the Ambrox series.

scholarly journals An acid catalyzed reversible ring-opening/ring-closure reaction involving a cyano-rhodamine spirolactam

2013 ◽  
Vol 11 (11) ◽  
pp. 1805 ◽  
Author(s):  
Honglin Li ◽  
Hong Guan ◽  
Xinrui Duan ◽  
Jun Hu ◽  
Guiren Wang ◽  
...  
Keyword(s):  
Ring Opening ◽  
Ring Closure ◽  
Acid Catalyzed

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.

ChemInform Abstract: Synthesis of Functionalized Cyclophanes by Ring-Opening/Ring-Closure Cascade Reactions of Siloxycyclopropanes.

ChemInform ◽  
2010 ◽  
Vol 30 (21) ◽  
pp. no-no
Author(s):  
Astrid Ullmann ◽  
Margit Gruner ◽  
Hans-Ulrich Reissig
Keyword(s):  
Ring Opening ◽  
Cascade Reactions ◽  
Ring Closure

ChemInform Abstract: Ring Opening Ring Closure Reactions with 3-Substituted Chromones under Nucleophilic Conditions

ChemInform ◽  
2015 ◽  
Vol 46 (50) ◽  
pp. no-no
Author(s):  
Magdy A. Ibrahim ◽  
Nasser M. El-Gohary ◽  
Sara Said
Keyword(s):  
Ring Opening ◽  
Ring Closure
Sign in / Sign up

Export Citation Format

Share Document