Short syntheses of the tricyclic indole alkaloids cimitrypazepine and fargesine

[Display omitted] •Syntheses of the alkaloids cimitrypazepine and fargesine are presented.•6-Hydroxy-2-iodo-3-nitrobenzaldehyde served as the starting point of the syntheses.•A Heck reaction and a reductive N-heterocyclization were used as key steps. A short synthetic sequence leading to the tricycl...

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Bibliographic Details
Published inTetrahedron letters Vol. 57; no. 34; pp. 3873 - 3876
Main Authors Ghimire, Ganesh, Söderberg, Björn C.G.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 24.08.2016
Elsevier
Subjects
Chemistry
Chemistry, Organic
Cimitrypazepine
Fargesine
Indole alkaloids
Palladium catalysis
Physical Sciences
Reductive N-heterocyclization
Science & Technology
Cimitrypazepine
Fargesine
Palladium catalysis
Indole alkaloids
Reductive N-heterocyclization
BIOMIMETIC SYNTHESIS
ENANTIOSELECTIVE SYNTHESIS
FORMAL SYNTHESIS
ERGOT ALKALOIDS
(-)-CIS-CLAVICIPITIC ACID
(+/-)-AURANTIOCLAVINE
PALLADIUM-CATALYZED SYNTHESIS
4-SUBSTITUTED INDOLES
CHEMISTRY
CLAVICIPITIC ACID
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Summary:[Display omitted] •Syntheses of the alkaloids cimitrypazepine and fargesine are presented.•6-Hydroxy-2-iodo-3-nitrobenzaldehyde served as the starting point of the syntheses.•A Heck reaction and a reductive N-heterocyclization were used as key steps. A short synthetic sequence leading to the tricyclic alkaloids cimitrypazepine and fargesine is reported. An intramolecular Heck reaction and a palladium catalyzed reductive N-heterocyclization are key steps in the synthesis.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2016.07.061