2-Dienylphenacyloxazolones and an intramolecular Diels–Alder approach to the A–B–C ring system of phenanthridone alkaloids

A general route to the A–B–C ring system of phenanthridone alkaloids is available by acylation of 2-oxa-zolone with a 2-butadienylbenzoic acid derivative, followed by an intramolecular Diels–Alder reaction and hydrolysis. A general route to the A–B–C ring system of phenanthridone alkaloids is availa...

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Bibliographic Details
Published in:Tetrahedron 2009-10, Vol.65 (43), p.8781-8785
Main Authors: Gaenzler, Faith Corbo, Guo, Chen (Lisa), Zhang, Yun-Wei, Azab, Mohammad E., Salem, Mounir A.I., Fan, Dong Ping, Smith, Michael B.
Format: Article
Language:English
Subjects:
Alkaloid
Diels–Alder
Oxazolone
Phenanthridones
Synthesis
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Summary:A general route to the A–B–C ring system of phenanthridone alkaloids is available by acylation of 2-oxa-zolone with a 2-butadienylbenzoic acid derivative, followed by an intramolecular Diels–Alder reaction and hydrolysis. A general route to the A–B–C ring system of phenanthridone alkaloids is available by acylation of 2-oxazolone with a 2-butadienylbenzoic acid derivative, followed by an intramolecular Diels–Alder reaction and hydrolysis. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2009.08.066