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Synthesis 2012(1): 125-129
DOI: 10.1055/s-0031-1289627
DOI: 10.1055/s-0031-1289627
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New YorkSynthesis of a Phenanthridine Analogue of Natural Isocarbostyril Alkaloids
Weitere Informationen
Received
27 September 2011
Publikationsdatum:
01. Dezember 2011 (online)
Publikationsverlauf
Publikationsdatum:
01. Dezember 2011 (online)

Abstract
A phenanthridine alkaloid analogue has been synthesized by a short sequence, using a stereoselective hydroxylation process and a Pictet-Spengler reaction. The starting material, 5-(3,4-dimethoxyphenyl)-6-nitrocyclohex-2-enol, is a compound previously reported by us and prepared through a Diels-Alder reaction. The configurational assignment of the starting material, previously done by NMR experiments, was confirmed by X-ray crystallographic analysis.
Key words
phenanthridine alkaloids - stereoselective hydroxylation - Pictet-Spengler reaction - heterocycles - cyclizations
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