Synthesis 2013; 45(2): 237-245
DOI: 10.1055/s-0032-1317928
paper
© Georg Thieme Verlag Stuttgart · New York

Highly Regio- and Stereoselective Synthesis of Tetracyclic Indoleno­isoxazolidines via Intramolecular 1,3-Dipolar Nitrone Cycloadditions

Manickam Bakthadoss*
a   Department of Organic Chemistry, University of Madras, Guindy Campus, Chennai, 600 025, India   Fax: +91(44)22352494   Email: bhakthadoss@yahoo.com
b   Department of Chemistry, Pondicherry University, Pondicherry 605 014, India
,
Govindan Sivakumar
a   Department of Organic Chemistry, University of Madras, Guindy Campus, Chennai, 600 025, India   Fax: +91(44)22352494   Email: bhakthadoss@yahoo.com
,
Duddu S. Sharada
c   Department of Chemistry, Indian Institute of Technology, Hyderabad 502 205, India
› Author Affiliations
Further Information

Publication History

Received: 17 October 2012

Accepted after revision: 27 November 2012

Publication Date:
13 December 2012 (online)


Abstract

A facile method for the simple synthesis of tetracyclic indoloisoxazolidine­ frameworks from Baylis–Hillman derivatives through formation of nitrones in situ followed by an intramolecular [3+2]-dipolar cycloaddition reaction sequence is described. High regio- and stereoselectivity, excellent yields, together with the creation of two rings and three contiguous stereogenic centers including one all carbon quaternary center, are the salient features of the present method.

Supporting Information

 
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