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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 33, 2003 - Issue 9
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Original Articles

A Stereospecific Approach to cis-anti-cis Triquinanes

A. Srikrishna Department of Organic Chemistry, Indian Institute of Science, Bangalore, IndiaCorrespondence[email protected]
,
T. Jagadeeshwar Reddy Department of Organic Chemistry, Indian Institute of Science, Bangalore, India
,
N. Palani Department of Chemistry, Indian Institute of Technology, Chennai, India
&
K. K. Balasubramanian Department of Chemistry, Indian Institute of Technology, Chennai, India
Pages 1537-1544 | Received 04 Apr 2002, Published online: 16 Aug 2006
 
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Abstract

A methodology for the synthesis of compounds containing the cis-anti-cis fused triquinane system has been developed starting from tricyclo[5.2.1.02,6]deca-4,8-dien-3-(exo)ol 6 involving Ireland ester Claisen rearrangement and intramolecular diazo ketone cyclopropanation reactions as key steps.

Acknowledgments

We thank the Head, R.S.I.C., I.I.T., Madras for NMR and mass spectra of some of the compounds. N.P. is grateful to Prof. T. R. Govindachari and Dr. S. Narasimhan, Centre for Agrochemical Research, SPIC Science Foundation, Madras for their encouragement. T.J.R is grateful to the University Grants Commission, New Delhi for the award of a research fellowship.

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