Synthesis 2008(13): 2134-2140  
DOI: 10.1055/s-2008-1067124
PAPER
© Georg Thieme Verlag Stuttgart · New York

Stereocontrolled Synthesis of Novel Spirocyclic Oxa-Bridged Cyclooctanoids through Sequential Transformations of Pentafulvenes

K. Syam Krishnana, Jinesh M. Kuthanappillila, Jubi Johna, C. H. Sureshb, E. Sureshc, K. V. Radhakrishnan*a
a Organic Chemistry Section, Chemical Sciences & Technology Division, National Institute for Interdisciplinary Science and Technology, (CSIR), Trivandrum 695019, Kerala, India
b Computer Modeling and Simulation Section, National Institute for Interdisciplinary Science and Technology, (CSIR), Trivandrum 695019, Kerala, India
Fax: +91(471)2491712; e-Mail: radhupreethi@rediffmail.com;
c Analytical Sciences Discipline, Central Salt and Marine Chemicals Research Institute, Bhavnagar 364002, Gujarat, India
Further Information

Publication History

Received 31 March 2008
Publication Date:
11 June 2008 (online)

Abstract

A novel and efficient methodology for the stereocontrolled synthesis of spirocyclic oxa-bridged cyclooctanoids having multiple spiro centers is described. The cycloaddition reaction, which affords spirocyclic cyclooctanoids is highly sterospecific and has been supported by theoretical calculations.

7

Crystallographic data for 7a have been deposited with the Cambridge Crystallographic Data Center as supplementary publication number CCDC 644182. Copies of the data may be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK (fax: +44 1223 33603 or e-mail: deposit@ccdc.cam.ac.uk).