Metathesis reactions for the synthesis of ring-fused carbazoles

Stephen C Pelly; Christopher J Parkinson; Willem A L van Otterlo; Charles B de Koning

doi:10.1021/jo051826s

Metathesis reactions for the synthesis of ring-fused carbazoles

J Org Chem. 2005 Dec 9;70(25):10474-81. doi: 10.1021/jo051826s.

Authors

Stephen C Pelly¹, Christopher J Parkinson, Willem A L van Otterlo, Charles B de Koning

Affiliation

¹ Molecular Sciences Institute, School of Chemistry, University of the Witwatersrand, P.O. Wits, 2050 South Africa.

PMID: 16323860
DOI: 10.1021/jo051826s

Abstract

[reactions: see text] The metathesis reaction is used as a key step for the synthesis of the indolo[2,3-a]carbazole core of rebeccamycin 13 and the sulfur analog of furostifoline 21. Using the same methodology for the attempted synthesis of furostifoline, we unexpectedly formed tert-butyl-2a-methyl-1,2,2a,10c-tetrahydro-6H-cyclobuta[c]furo[3,2-a]carbazole-6-carboxylate 26 from the unstable diene, tert-butyl 2-(2-isopropenyl-3-furyl)-3-vinyl-1H-indole-1-carboxylate 25, presumably via a spontaneous pi8 electrocyclization reaction.

Publication types

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

MeSH terms

Carbazoles / chemical synthesis*
Cyclization
Indoles / chemical synthesis
Magnetic Resonance Spectroscopy

Substances

Carbazoles
Indoles
rebeccamycin