Issue 56, 2016

Rhodium-catalyzed cycloaddition of carbonyl ylides for the synthesis of spiro[furo[2,3-a]xanthene-2,3′-indolin]-2′-one scaffolds

Abstract

An intramolecular cycloaddition of oxonium ylides generated from 3-diazooxindole and a bifunctional substrate i.e. 2-methyl-2-(4-methylpent-3-en-1-yl)-2H-chromene-3-carbaldehyde has been achieved using 5 mol% of Rh2(OAc)4 to produce highly substituted 3,3,5a-trimethyl-3a,5,5a,11b-tetrahydro-3H,4H-spiro[furo[2,3-a]xanthene-2,3′-indolin]-2′-ones in good yields with high diastereoselectivity. This is the first example of the synthesis of biologically relavant polycyclic frameworks from readily accessible precursors.

Graphical abstract: Rhodium-catalyzed cycloaddition of carbonyl ylides for the synthesis of spiro[furo[2,3-a]xanthene-2,3′-indolin]-2′-one scaffolds

Associated articles

Supplementary files

Article information

Article type
Paper
Submitted
03 मार्च 2016
Accepted
10 मई 2016
First published
12 मई 2016

RSC Adv., 2016,6, 50497-50499

Rhodium-catalyzed cycloaddition of carbonyl ylides for the synthesis of spiro[furo[2,3-a]xanthene-2,3′-indolin]-2′-one scaffolds

B. V. S. Reddy, E. P. Reddy, B. Sridhar and Y. J. Rao, RSC Adv., 2016, 6, 50497 DOI: 10.1039/C6RA05661J

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