Synthesis of tetracyclic spiroindolines by an interrupted Bischler–Napieralski reaction: total synthesis of akuammicine. Issue 44 (1st November 2021)

• Record Type: Journal Article
• Authors: Faltracco, Matteo; Ruijter, Eelco
• Is Part Of: Organic & biomolecular chemistry. Volume 19:Issue 44(2021)
• Page Start: 9641
• Page End: 9644
• Publication Date: 2021-11-01
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d1ob01966j
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : The interrupted Bischler–Napieralski reaction of β, γ-unsaturated tryptamides affords tetracyclic spiro pyrroloindolines, which can be used in the total synthesis of the Strychnos alkaloid, akuammicine. Abstract : Judicious substrate design allows interruption of the classical Bischler–Napieralski reaction, providing access to a range of diversely substituted tetracyclic spiroindolines. These complex polycyclic scaffolds are valuable building blocks for the construction of indole alkaloids, as showcased in a concise total synthesis of (±)-akuammicine.