Issue 22, 2015

A regioselective facile synthesis of furo[3,4-b]carbazolones: application to the total synthesis of mafaicheenamine E and claulansine D

Abstract

1-Hydroxycarbazole-2,3-dicarboxylates have been shown to undergo chemoselective reductive cyclization to furo[3,4-b]carbazolones on reaction with LiAlH4. One of the furocarbazolones is utilized to accomplish the first total synthesis of claulansine D and mafaicheenamine E in 9 and 6 steps respectively. The other key steps of the syntheses are addition of an allylic indium reagent and CC double bond isomerization.

Graphical abstract: A regioselective facile synthesis of furo[3,4-b]carbazolones: application to the total synthesis of mafaicheenamine E and claulansine D

Supplementary files

Article information

Article type
Paper
Submitted
23 Mar 2015
Accepted
28 Apr 2015
First published
28 Apr 2015

Org. Biomol. Chem., 2015,13, 6344-6352

A regioselective facile synthesis of furo[3,4-b]carbazolones: application to the total synthesis of mafaicheenamine E and claulansine D

D. Mal and J. Roy, Org. Biomol. Chem., 2015, 13, 6344 DOI: 10.1039/C5OB00575B

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