Total synthesis of 7- and 8-oxygenated pyrano[3,2-a]carbazole and pyrano[2,3-a]carbazole alkaloids via boronic acid-catalyzed annulation of the pyran ring

Konstanze K Julich-Gruner; Olga Kataeva; Arndt W Schmidt; Hans-Joachim Knölker

doi:10.1002/chem.201403143

Total synthesis of 7- and 8-oxygenated pyrano[3,2-a]carbazole and pyrano[2,3-a]carbazole alkaloids via boronic acid-catalyzed annulation of the pyran ring

Chemistry. 2014 Jul 7;20(28):8536-40. doi: 10.1002/chem.201403143. Epub 2014 May 30.

Authors

Konstanze K Julich-Gruner¹, Olga Kataeva, Arndt W Schmidt, Hans-Joachim Knölker

Affiliation

¹ Department of Chemistry, Technische Universität Dresden, Bergstrasse 66, 01069 Dresden (Germany), Fax: (+49) 351-463-37030.

PMID: 24889600
DOI: 10.1002/chem.201403143

Abstract

The boronic acid-catalyzed annulation of citral opens up a short route to oxygenated cyclized monoterpenoid pyranocarbazole alkaloids. Thus, murrayamine-D is available in only three steps and 55% overall yield from the corresponding carbazole precursor.

Keywords: CH bond activation; alkaloids; natural products; palladium; stereoselective catalysis.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkaloids / chemical synthesis*
Boronic Acids / chemistry*
Carbazoles / chemical synthesis*
Carbazoles / chemistry*
Catalysis
Cyclization
Molecular Structure
Pyrans
Stereoisomerism

Substances

Alkaloids
Boronic Acids
Carbazoles
Pyrans
carbazole