Titanium(IV)-Promoted Regioselective Nucleophilic Ring-Opening Reaction of Chiral Epoxyallyl Alcohols with Acids as a Tool for Ready Access to Chiral 1,2,3-Triol Monoesters: Application to Stereoselective Total Synthesis of Macrolides

2011 ◽  
Vol 77 (1) ◽  
pp. 674-679 ◽  
Author(s):  
Palakodety Radha Krishna ◽  
D. Venkata Ramana
Keyword(s):  
Total Synthesis ◽  
Ring Opening ◽  
Ring Opening Reaction ◽  
Ready Access ◽  
Nucleophilic Ring Opening

Regioselective nucleophilic ring-opening reaction of chiral epoxyallyl alcohols: a ready access to the pyran core of macrolactin 3

2014 ◽  
Vol 55 (22) ◽  
pp. 3381-3383 ◽  
Author(s):  
Palakodety Radha Krishna ◽  
Rajesh Nomula ◽  
Kallaganti V.S. Rama Krishna
Keyword(s):  
Ring Opening ◽  
Ring Opening Reaction ◽  
Ready Access ◽  
Nucleophilic Ring Opening

scholarly journals (1R,4S,5S)-5-((3-Hydroxypropyl)amino)-4-((1-Methyl-1H-tetrazol-5-yl)thio)Cyclopent-2-en-1-ol

Molbank ◽  
10.3390/m1199 ◽  
2021 ◽  
Vol 2021 (2) ◽  
pp. M1199
Author(s):  
Milene A. G. Fortunato ◽  
Filipa Siopa ◽  
Carlos A. M. Afonso
Keyword(s):  
Spectral Data ◽  
13C Nmr ◽  
Ring Opening ◽  
Environmentally Friendly ◽  
Mass Spectral Data ◽  
Mass Spectral ◽  
Excellent Yield ◽  
Ring Opening Reaction ◽  
Nucleophilic Ring Opening

Using environmentally friendly conditions, the nucleophilic ring-opening reaction of 6-azabicyclo[3.1.0]hex-3-en-2-ol with 1-methyl-1H-tetrazole-5-thiol provided a novel thiol-incorporated aminocyclopentitol, (1R,4S,5S)-5-((3-hydroxypropyl)amino)-4-((1-methyl-1H-tetrazol-5-yl)thio)cyclopent-2-en-1-ol, in excellent yield (95%). The newly synthesized compound was analyzed and characterized via 1H, 13C-NMR, HSQC, and mass spectral data.

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.

Origin of regioselectivity in nucleophilic ring-opening reaction of 4-trifluoroacetyl-1,3-oxazolium-5-olates

1998 ◽  
Vol 39 (34) ◽  
pp. 6189-6190 ◽  
Author(s):  
Masami Kawase ◽  
Hiromi Koiwai ◽  
Setsuo Saito ◽  
Teruo Kurihara
Keyword(s):  
Ring Opening ◽  
Ring Opening Reaction ◽  
Nucleophilic Ring Opening

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.

Asymmetric total synthesis of paecilomycin C through intramolecular nucleophilic ring opening of an epoxide

2019 ◽  
Vol 17 (31) ◽  
pp. 7369-7379 ◽  
Author(s):  
Joy Chakraborty ◽  
Samik Nanda
Keyword(s):  
Total Synthesis ◽  
Ring Opening ◽  
Asymmetric Total Synthesis ◽  
Naturally Occurring ◽  
Acid Lactone ◽  
Nucleophilic Ring Opening

An efficient asymmetric total synthesis of naturally occurring resorcylic acid lactone (RAL) paecilomycin C was achieved by employing carboxylate assisted 5-exo-tet ring opening of an epoxide as a key reaction.

Disulfides as mercapto-precursors in nucleophilic ring opening reaction of polymeric epoxides: establishing equimolar stoichiometric conditions in a thiol–epoxy ‘click’ reaction

2020 ◽  
Vol 56 (54) ◽  
pp. 7419-7422 ◽  
Author(s):  
Taejun Eom ◽  
Anzar Khan
Keyword(s):  
Ring Opening ◽  
Click Reaction ◽  
Ring Opening Reaction ◽  
Nucleophilic Ring Opening

This work establishes equimolar stoichiometric conditions in a thiol–epoxy ‘click’ reaction.

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