Premium
A Short and Efficient Synthesis of Iminosugar 2‐Acyl Indolizidine
Author(s) -
Chinthapally Kiran,
Karthik Reshamina,
Senthilkumar Soundararasu,
Baskaran Sundarababu
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201604376
Subject(s) - indolizidine , iminosugar , generality , combinatorial chemistry , chemistry , stereochemistry , organic chemistry , psychology , psychotherapist , alkaloid , enzyme
A facile and convergent approach has been developed for the stereoselective construction of biologically important polyhydroxylated 2‐acyl indolizidine framework using aza‐Cope rearrangement–Mannich cyclization as a key step. The generality of this methodology is demonstrated with various lactol‐tosylates derived from carbohydrates. The presented method provides an easy access to indolizidine‐ and tetrahydroindolizine‐based iminosugar derivatives in good yields.