Stereoselective Synthesis of C-Substituted Morpholine Derivatives using Reductive Etherification Reaction: Total Synthesis of Chelonin C

A general strategy is developed for the stereoselective synthesis of C-substituted morpholine derivatives using intramolecular reductive etherification reaction. The method is extended to the first stereoselective total synthesis of (±)-chelonin C.

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Bibliographic Details
Published in:Journal of organic chemistry 2011-12, Vol.76 (24), p.10325-10331
Main Authors: Gharpure, Santosh J, Prasad, J. V. K
Format: Article
Language:English
Subjects:
Biological Products - chemical synthesis
Bridged Bicyclo Compounds - chemical synthesis
Chemistry
Chemistry Techniques, Synthetic
Esterification
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
Magnetic Resonance Spectroscopy
Molecular Structure
Morpholines - chemical synthesis
Organic chemistry
Oxidation-Reduction
Preparations and properties
Spiro Compounds - chemical synthesis
Stereoisomerism
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Description
Summary:A general strategy is developed for the stereoselective synthesis of C-substituted morpholine derivatives using intramolecular reductive etherification reaction. The method is extended to the first stereoselective total synthesis of (±)-chelonin C.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo201975b