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Architecturally diverse heterocycle formation by N-acyliminium ion initiated cyclization

✍ Scribed by Matthew M Abelman; Jeffrey K Curtis; Donald R James

Book ID: 104253864
Publisher: Elsevier Science
Year: 2003
Tongue: French
Weight: 200 KB
Volume: 44
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(03)01190-0

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✦ Synopsis

Enaminoesters containing a tethered indole or aryl moiety on the amine react with substituted maleic anhydrides or acryloyl chlorides to provide pyrrolinone or dihydropyridone products, respectively. The indole-tethered dihydropyridones can be induced to undergo a one-pot cyclization whereas, the indole-tethered pyrrolinone intermediates are readily cyclized with HCl. The aryl-tethered pyrrolinones or dihydropyridones can be isolated and subsequently induced to cyclize with triflic acid. This methodology culminates in the synthesis of erythrane-like and other natural products that are readily amenable to combinatorial library production.

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