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Synthesis 2003(10): 1559-1564
DOI: 10.1055/s-2003-40529
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Chemoselective 1,3-Dipolar Cycloaddition Reactions of Rhodium(II)-Generated Isomünchnones with 1,4-Quinones: Synthesis of Novel Azapolycycles []

Vijay Nair*a, V. Santhia, K. C. Sheelaa, K. V. Radhakrishnana, Nigam P. Rathb
a Organic Chemistry Division, Regional Research Laboratory (CSIR), Trivandrum 695 019, India
Fax: 91(471)2491712; e-Mail: vijaynair_2001@yahoo.com ; e-Mail: gvn@csrrltrd.ren.nic.in;
b Department of Chemistry, University of Missouri, St. Louis, MO 63121-4499, USA
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Publication History

Received 7 January 2003
Publication Date:
08 July 2003 (online)

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Abstract

The formation of the hybrid skeletons of oxoprotoberberines and quinonoid natural products is achieved by the cycloaddition of isomünchnones with 1,4-quinones, followed by BF3˙OEt2-catalyzed transformation of the adducts.

Key words

hybrid compounds - oxoprotoberberines - isomünchnones - 1,4-quinones - cycloaddition

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AM1 calculations using PC SPARTAN Graphical Interface Package for Molecular Mechanics and Molecular Orbital Models by Wave functions Inc., 18401 von Karman, Suite 370, Irvine, California, 92612, USA.