Total Synthesis of Luotonin A and Rutaecarpine from an Aldimine via the Designed Cyclization

Se Hyun Kwon, Hong Ahn Seo, Cheol-Hong Cheon

Research output: Contribution to journalArticle

21 Citations (Scopus)

Abstract

The total synthesis of rutaecarpine (1) and luotonin A (2) is described through controlled cyclization of a common aldimine intermediate 5 derived from ethyl-2-aminocinnamate and quinazolinone-2-carbaldehyde. The cyanide-mediated imino-Stetter reaction of aldimine 5 provided the corresponding indole derivative 3, from which the total synthesis of rutaecarpine (1) was completed via the formation of a 6-membered C-ring. On the other hand, microwave-assisted thermal 6π-electrocyclization of the common intermediate 5, followed by the formation of a 5-membered C′-ring, allowed the completion of the total synthesis of luotonin A (2).

Original languageEnglish
Pages (from-to)5280-5283
Number of pages4
JournalOrganic Letters
Volume18
Issue number20
DOIs
Publication statusPublished - 2016 Oct 21

Fingerprint

Cyclization
Quinazolinones
Cyanides
synthesis
Microwaves
Hot Temperature
rings
indoles
cyanides
Derivatives
microwaves
luotonin A
rutecarpine
indole

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Total Synthesis of Luotonin A and Rutaecarpine from an Aldimine via the Designed Cyclization. / Kwon, Se Hyun; Seo, Hong Ahn; Cheon, Cheol-Hong.

In: Organic Letters, Vol. 18, No. 20, 21.10.2016, p. 5280-5283.

Research output: Contribution to journalArticle

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