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Synthesis 2021; 53(02): 359-364
DOI: 10.1055/s-0040-1706551
paper

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

Valerie Lösle
a   Faculty of Chemistry, Technische Universität Dresden, Bergstraße 66, 01069 Dresden, Germany   Email: hans-joachim.knoelker@tu-dresden.de
,
Olga Kataeva
b   A. E. Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, Arbuzov Str. 8, Kazan 420088, Russian Federation
,
Hans-Joachim Knölker∗
a   Faculty of Chemistry, Technische Universität Dresden, Bergstraße 66, 01069 Dresden, Germany   Email: hans-joachim.knoelker@tu-dresden.de
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Dedicated to Professor Tomáš Hudlický on the occasion of his 71st birthday

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.

Key words

carbazoles - alkaloids - annulation - catalysis - cyclization - natural products - total synthesis - palladium

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1706551.
  • Supporting Information


Publication History

Received: 07 September 2020

Accepted after revision: 06 October 2020

Article published online:
05 November 2020

© 2020. Thieme. All rights reserved

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