Article ; Online: Synthesis of (+/-)-likonide B (smenochromene D) using a regioselective Claisen rearrangement, separation of the enantiomers and stereochemical assignment.
Organic & biomolecular chemistry
2009 Volume 7, Issue 10, Page(s) 2127–2134
Abstract: ... smenochromene D and (+)-likonide B. ... A synthesis of the unusual ansa-bridged farnesyl hydroquinone derivative likonide B in racemic form ... is described. The natural product, also known as smenochromene D, was obtained from geranylacetone ...
Abstract | A synthesis of the unusual ansa-bridged farnesyl hydroquinone derivative likonide B in racemic form is described. The natural product, also known as smenochromene D, was obtained from geranylacetone by a route in which the key steps are a regioselective microwave-mediated Claisen rearrangement of an aryl propargyl ether to deliver the chromene ring, and macrocyclization via an intramolecular Mitsunobu reaction. Subsequent HPLC on a chiral stationary phase gave the pure (+)- and (-)-enantiomers, that were studied by CD spectroscopy, thereby shedding some light on the true stereochemical nature of the two natural products (-)-smenochromene D and (+)-likonide B. |
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MeSH term(s) | Biological Products/chemistry ; Hydroquinones/chemical synthesis ; Hydroquinones/chemistry ; Microwaves ; Molecular Structure ; Stereoisomerism |
Chemical Substances | Biological Products ; Hydroquinones ; likonide B |
Language | English |
Publishing date | 2009-05-21 |
Publishing country | England |
Document type | Journal Article |
ZDB-ID | 2097583-1 |
ISSN | 1477-0539 ; 1477-0520 |
ISSN (online) | 1477-0539 |
ISSN | 1477-0520 |
DOI | 10.1039/b901358j |
Database | MEDical Literature Analysis and Retrieval System OnLINE |
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