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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Bibliographische Detailangaben
Veröffentlicht in:	Journal of organic chemistry 2011-12, Vol.76 (24), p.10325-10331
Hauptverfasser:	Gharpure, Santosh J, Prasad, J. V. K
Format:	Artikel
Sprache:	eng
Schlagworte:	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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Beschreibung
Zusammenfassung:	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