Construction of the Six- and Five-Membered Aza-Heterocyclic Units of the Isoindoloisoquinolone Nucleus by Parham-Type Cyclization Sequences –Total Synthesis of Nuevamine

✍ Scribed by Anne Moreau; Axel Couture; Eric Deniau; Pierre Grandclaudon

• Publisher: John Wiley and Sons
• Year: 2005
• Tongue: English
• Weight: 111 KB
• Volume: 2005
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/ejoc.200500312

✦ Synopsis

Abstract

An efficient methodology for the synthesis of isoindolo[1,2‐a]isoquinolones based on two Parham‐type cyclizations allowing the formation of the five‐ and six‐membered nitrogenated rings from carbamate or diacylamine precursors is described. The synthetic potential of this method has been further illustrated by the total synthesis of the alkaloid nuevamine. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)