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Nucleophilic addition to chiral pyridinium salts: stereoselective synthesis of (−)-Na-methylervitsine

✍ Scribed by M.-Lluı̈sa Bennasar; Ester Zulaica; Yolanda Alonso; Joan Bosch

Book ID
104359633
Publisher
Elsevier Science
Year
2003
Tongue
English
Weight
276 KB
Volume
14
Category
Article
ISSN
0957-4166

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✦ Synopsis

Chiral non-racemic 4-substituted 3,5-diacyl-1,4-dihydropyridines 8 are prepared by the regio-and diastereoselective addition of organocopper reagents to chiral pyridinium salt 2, followed by acylation with trichloroacetic anhydride and subsequent haloform reaction. Additionally, (-)-N a -methylervitsine is synthesized by reaction of the enolate derived from 2-acetylindole 9 with pyridinium salt 2, followed by electrophile (Me 2 N + CH 2 I -)-induced cyclization and subsequent elaboration of the 16-methylene and (20E)-ethylidene substituents.

📜 SIMILAR VOLUMES

ChemInform Abstract: Nucleophilic Additi
ChemInform Abstract: Nucleophilic Addition of 1-Acetylindole Enolates to Pyridinium Salts. Stereoselective Formal Synthesis of (.+-.)-Geissoschizine and (.+-.)-Akagerine via 1,4-Dihydropyridines.
✍ M.-Lluisa Bennasar; Juan-Miguel Jimenez; Bernat Vidal; Bilal A. Sufi; Joan Bosch 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 38 KB 👁 2 views

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