First Total Synthesis and Investigation of the X-ray Crystal Structure of the Pyrano[3,2- a ]carbazole Alkaloid Clausenalansine A

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Contributors

Abstract

We describe the first total synthesis of the recently discovered pyrano[3,2- a ]carbazole alkaloid clausenalansine A. The synthetic strategy for the construction of this formylpyrano[3,2- a ]carbazole is based on a sequence of Buchwald-Hartwig coupling, palladium(II)-catalyzed oxidative cyclization, Lewis acid promoted annulation of the pyran ring, and chemoselective oxidation of a methyl to a formyl group.

Details

Original languageEnglish
Pages (from-to)359-364
Number of pages6
JournalSynthesis (Germany)
Volume53
Issue number2
Publication statusPublished - 19 Jan 2021
Peer-reviewedYes

Keywords

ASJC Scopus subject areas

Keywords

  • alkaloids, annulation, carbazoles, catalysis, cyclization, natural products, palladium, total synthesis