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 language | English |
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Pages (from-to) | 5280-5283 |
Number of pages | 4 |
Journal | Organic Letters |
Volume | 18 |
Issue number | 20 |
DOIs | |
Publication status | Published - 2016 Oct 21 |
ASJC Scopus subject areas
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry