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Straightforward synthesis of indolizidine alkaloid 167B

✍ Scribed by Stéphanie Gracia; Rudolf Jerpan; Stéphane Pellet-Rostaing; Florence Popowycz; Marc Lemaire

Book ID
104098381
Publisher
Elsevier Science
Year
2010
Tongue
French
Weight
421 KB
Volume
51
Category
Article
ISSN
0040-4039

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✦ Synopsis

The synthetic access to indolizidines, substituted in C-5 position, was reported with good diastereoselectivity. The strategy developed was based on a key step of Michael addition associated with a Clauson-Kaas condensation.

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An Expeditious Synthesis of the Dendroba
An Expeditious Synthesis of the Dendrobatid Indolizidine Alkaloid 167B
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Synthesis of Indolizidine 167B.
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## Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

Enantioselective synthesis of (−)-indoli
Enantioselective synthesis of (−)-indolizidine 167B
✍ Pierre Chalard; Roland Remuson; Yvonne Gelas-Mialhe; Jean-Claude Gramain; Isabel 📂 Article 📅 1999 🏛 Elsevier Science 🌐 French ⚖ 187 KB

The enantioselective total synthesis of (-)-indolizidine 167B is described. The key step is the intramolecular cyclization of the chiral N-acyliminium ion 6. Indolizidine 167B was obtained in 7 steps and 17% yield from ethyl (R)-3-aminohexanoate, with an enantiomeric excess of 93%.