Stereoselective synthesis of O-tosyl azabicyclic derivatives via aza Prins reaction of endocyclic N-acyliminium ions: application to the total synthesis of (±)-epi-indolizidine 167B and 209D

2014 ◽  
Vol 12 (36) ◽  
pp. 7026-7035 ◽  
Author(s):  
Anil K. Saikia ◽  
Kiran Indukuri ◽  
Jagadish Das
Keyword(s):  
Total Synthesis ◽  
Stereoselective Synthesis ◽  
Cyclization Reaction ◽  
Diastereoselective Synthesis ◽  
Prins Reaction ◽  
Prins Cyclization ◽  
Acyliminium Ions

A diastereoselective synthesis of 4-O-tosyl piperidine containing azabicyclic derivatives has been established via Prins cyclization reaction. This protocol has been applied for the total synthesis of (±)-epi-indolizidine 167B and 209D.

scholarly journals Prins cyclization-mediated stereoselective synthesis of tetrahydropyrans and dihydropyrans: an inspection of twenty years

2021 ◽  
Vol 17 ◽  
pp. 932-963
Author(s):  
Asha Budakoti ◽  
Pradip Kumar Mondal ◽  
Prachi Verma ◽  
Jagadish Khamrai
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Stereoselective Synthesis ◽  
Building Blocks ◽  
Active Pharmaceutical Ingredients ◽  
Prins Reaction ◽  
Prins Cyclization ◽  
Pharmaceutical Ingredients ◽  
New Strategies ◽  
Made In

Functionalized tetrahydropyran (THP) rings are important building blocks and ubiquitous scaffolds in many natural products and active pharmaceutical ingredients (API). Among various established methods, the Prins reaction has emerged as a powerful technique in the stereoselective synthesis of the tetrahydropyran skeleton with various substituents, and the strategy has further been successfully applied in the total synthesis of bioactive macrocycles and related natural products. In this context, hundreds of valuable contributions have already been made in this area, and the present review is intended to provide the systematic assortment of diverse Prins cyclization strategies, covering the literature reports of the last twenty years (from 2000 to 2019), with an aim to give an overview on exciting advancements in this area and designing new strategies for the total synthesis of related natural products.

Design, Prins-cyclization reaction promoting diastereoselective synthesis of 10 new tetrahydropyran derivatives and in vivo antinociceptive evaluations

2012 ◽  
Vol 58 ◽  
pp. 1-11 ◽  
Author(s):  
Saulo L. Capim ◽  
Paulo H.P. Carneiro ◽  
Paloma C. Castro ◽  
Maithê R.M. Barros ◽  
Bruno G. Marinho ◽  
...  
Keyword(s):  
Cyclization Reaction ◽  
Diastereoselective Synthesis ◽  
Prins Cyclization

scholarly journals Stereoselective Synthesis of 4-O-Tosyltetrahydropyrans via Prins Cyclization Reaction of Enol Ethers

SynOpen ◽  
2019 ◽  
Vol 03 (01) ◽  
pp. 36-45
Author(s):  
Sujit Sarkar ◽  
Namita Devi ◽  
Bikoshita Porashar ◽  
Santu Ruidas ◽  
Anil Saikia
Keyword(s):  
Intramolecular Cyclization ◽  
Stereoselective Synthesis ◽  
Cyclization Reaction ◽  
Prins Cyclization ◽  
Enol Ethers ◽  
Toluenesulfonic Acid

Intramolecular cyclization of enol ethers mediated by para-toluenesulfonic acid leads to substituted tetrahydropyrans in good to moderate yields. The reaction is diastereoselective.

Diastereoselective Synthesis of Substituted Tetrahydrothiophenes and -thiopyrans via Thia-Prins Cyclization Reaction

2015 ◽  
Vol 80 (5) ◽  
pp. 2641-2648 ◽  
Author(s):  
Madhurjya Borah ◽  
Paramartha Gogoi ◽  
Kiran Indukuri ◽  
Anil K. Saikia
Keyword(s):  
Cyclization Reaction ◽  
Diastereoselective Synthesis ◽  
Prins Cyclization

ChemInform Abstract: Diastereoselective Synthesis of Substituted Tetrahydrothiophenes and -thiopyrans via Thia-Prins Cyclization Reaction.

ChemInform ◽  
2015 ◽  
Vol 46 (29) ◽  
pp. no-no
Author(s):  
Madhurjya Borah ◽  
Paramartha Gogoi ◽  
Kiran Indukuri ◽  
Anil K. Saikia
Keyword(s):  
Cyclization Reaction ◽  
Diastereoselective Synthesis ◽  
Prins Cyclization

Stereoselective synthesis of 1,6-dioxaspirolactones from spiro-cyclopropanecarboxylated sugars: total synthesis of dihydro-pyrenolide D

RSC Advances ◽  
2015 ◽  
Vol 5 (11) ◽  
pp. 8142-8145 ◽  
Author(s):  
Bandi Ramakrishna ◽  
Perali Ramu Sridhar
Keyword(s):  
Total Synthesis ◽  
Stereoselective Synthesis ◽  
Cyclization Reaction ◽  
One Pot ◽  
Ring Enlargement

A one-pot protocol for the stereoselective construction of γ-spiroketal γ-lactone frameworks from sugar derived spiro-cyclopropanecarboxylic acids involving a ring enlargement and cyclization reaction is revealed.

Sign in / Sign up

Export Citation Format

Share Document