A Short Synthesis of (±)-13-Deoxyserratine

A Short Synthesis of (±)-13-Deoxyserratine

A short and efficient total synthesis of (±)‐13‐deoxyserratine (3) features a highly stereoselective intramolecular Pauson–Khand reaction of 1 and a cascade of radical cyclizations starting with the amidyl radical 2. The desired alkaloid 3 was thus obtained in ten steps in an overall yield of 12 %....

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Veröffentlicht in:Angewandte Chemie International Edition 2002-05, Vol.41 (10), p.1783-1785
Hauptverfasser: Cassayre, Jérome, Gagosz, Fabien, Zard, Samir Z.
Format: Artikel
Sprache:eng
Schlagworte:
alkaloids
Alkaloids - chemistry
Chemical Sciences
Chemistry, Organic - methods
Free Radicals
Heterocyclic Compounds, 4 or More Rings - chemical synthesis
Heterocyclic Compounds, 4 or More Rings - chemistry
indolizidines
Lycopodium - metabolism
Models, Chemical
Nitrogen - chemistry
Organic chemistry
Pauson-Khand reaction
radical reactions
Stereoisomerism
total synthesis
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Beschreibung
Zusammenfassung:A short and efficient total synthesis of (±)‐13‐deoxyserratine (3) features a highly stereoselective intramolecular Pauson–Khand reaction of 1 and a cascade of radical cyclizations starting with the amidyl radical 2. The desired alkaloid 3 was thus obtained in ten steps in an overall yield of 12 %. THP=tetrahydropyranyl, TBS=tert‐butyldimethylsilyl.
ISSN:1433-7851
1521-3773
DOI:10.1002/1521-3773(20020517)41:10<1783::AID-ANIE1783>3.0.CO;2-I