Synlett 2012; 23(12): 1769-1774
DOI: 10.1055/s-0031-1290380
letter
© Georg Thieme Verlag Stuttgart · New York

Lateral Lithiation-Initiated Annulations in the Synthesis of 1-Oxygenated Carbazole Alkaloids and a Cycloheptacarbazole

Amit Kumar Jana
a  Department of Chemistry, Indian Institute of Technology, Kharagpur 721302, India, Email: dmal@chem.iitkgp.ernet.in
,
Pallab Pahari
a  Department of Chemistry, Indian Institute of Technology, Kharagpur 721302, India, Email: dmal@chem.iitkgp.ernet.in
,
Dipakranjan Mal*
a  Department of Chemistry, Indian Institute of Technology, Kharagpur 721302, India, Email: dmal@chem.iitkgp.ernet.in
› Author Affiliations
Further Information

Publication History

Received: 31 March 2012

Accepted after revision: 23 April 2012

Publication Date:
21 June 2012 (online)


Abstract

Anionic [4+2] annulation of lithiated furoindolones with dimethyl maleate followed by selective demethoxycarbonylation provides an efficient synthetic route to 3-methoxycarbonylcarbazoles. The route has led to the straightforward synthesis of two natural products, namely clausine E, mukonine, and their 4-prenyl analogues. A new route to cyclohepta[d,e,f]carbazole was also uncovered during the investigations.

Supporting Information

 
  • References and Notes

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