Synthesis 2018; 50(13): 2516-2522
DOI: 10.1055/s-0037-1609717
paper
© Georg Thieme Verlag Stuttgart · New York

First Total Synthesis of 7-Isovaleryloxy-8-methoxygirinimbine

Christian Brütting
a   Fakultät Chemie, Technische Universität Dresden, Bergstraße 66, 01069 Dresden, Germany   Email: hans-joachim.knoelker@tu-dresden.de
,
Arndt W. Schmidt
a   Fakultät Chemie, Technische Universität Dresden, Bergstraße 66, 01069 Dresden, Germany   Email: hans-joachim.knoelker@tu-dresden.de
,
Olga Kataeva
b   A. M. Butlerov Chemistry Institute, Kazan Federal University, Kremlevskaya Str. 18, Kazan 420008, Russian Federation
,
Hans-Joachim Knölker*
a   Fakultät Chemie, Technische Universität Dresden, Bergstraße 66, 01069 Dresden, Germany   Email: hans-joachim.knoelker@tu-dresden.de
› Author Affiliations
Further Information

Publication History

Received: 27 February 2018

Accepted after revision: 26 March 2018

Publication Date:
19 April 2018 (online)


Abstract

We describe the first total synthesis of the pyrano[3,2-a]carbazole alkaloid 7-isovaleryloxy-8-methoxygirinimbine, using a palladium(II)-catalyzed double C–H-bond activation for construction of the carbazole framework and a phenylboronic acid catalyzed annulation of the pyran ring as key steps.

Supporting Information