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.

    References

  • 1a Brito I. Cueto M. Diaz-Marrero AR. Parias J. Martin AS. J. Nat. Prod.  2002,  65:  946 
  • 1b Conroy H. Chakrabarti JK. Tetrahedron  1959,  4:  6 
  • 1c Cui CB. Kakeya H. Osada H. Tetrahedron  1996,  52:  12651 
  • 1d Cui CB. Kakeya H. Osada H. J. Antibiot.  1996,  49:  832 
  • 1e Cui CB. Kakeya H. Osada H. Tetrahedron  1997,  53:  59 
  • 1f Daly JW. Karle I. Myers C. Tokuyama T. Waters JA. Witkop B. Proc. Natl. Acad. Sci. U.S.A.  1971,  68:  1870 
  • 1g Okabe KJ. Yamada K. Yamamura S. Takasa SJ. J. Chem. Soc. C  1967,  2201 
  • 1h Sakabe N. Takada S. Okabe KJ. J. Chem. Soc., Chem. Commun.  1967,  259 
  • 2a Efange SMN. Kamath AP. Khare AB. Kung M.-P. Mach RH. Parsons SMN. J. Med. Chem.  1997,  40:  3905 
  • 2b Goehring RR. Org. Prep. Proced. Int.  1995,  27:  691 
  • 2c Edmondson S. Danishefsky SJ. Sepp-Lorenzino I. Rosen N. J. Am. Chem. Soc.  1999,  121:  2147 
  • 3a Alper PB. Meyers C. Lerchner A. Siegel DR. Carreira EM. Angew. Chem. Int. Ed.  1999,  38:  3186 
  • 3b Trost BM. Yong B. Miller ML. J. Am. Chem. Soc.  1989,  111:  6482 
  • 4a Pages L. Llebaria A. Camps F. Molins E. Miravitlles C. Moreto JM. J. Am. Chem. Soc.  1992,  114:  10449 
  • 4b Oda M. Fukuta A. Kajioka T. Uchiyama T. Kainuma H. Miyatake R. Kuroda S. Tetrahedron  2000,  56:  9917 
  • 5a Anas S. Krishnan KS. Sajisha VS. Anju KS. Radhakrishnan KV. Suresh E. Suresh CH. New J. Chem.  2007,  31:  237 
  • 5b Radhakrishnan KV. Anas S. Suresh E. Koga N. Suresh CH. Bull. Chem. Soc. Jpn.  2007,  80:  484 
  • 5c Anas S. Sajisha VS. Mohanlal S. Radhakrishnan KV. Synlett  2006,  2399 
  • 5d Nair V. Jayan CN. Radhakrishnan KV. Anilkumar G. Rath NP. Tetrahedron  2001,  57:  5807 
  • 6a Radhakrishnan KV. Krishnan KS. Bhadbhade MM. Bhosekar GV. Tetrahedron Lett.  2005,  46:  4785 
  • 6b Krishnan KS. Sajisha VS. Anas S. Suresh CH. Bhadbhade MM. Bhosekar GV. Radhakrishnan KV. Tetrahedron  2006,  62:  5952 
  • 6c Krishnan KS. Suresh E. Mathew S. Radhakrishnan KV. Synthesis  2006,  1811 
  • 6d Krishnan KS. Smitha M. Suresh E. Radhakrishnan KV. Tetrahedron  2006,  62:  12345 
  • 6e Krishnan KS. Kuthanapillil JM. Rajan R. Suresh E. Radhakrishnan KV. Eur. J. Org. Chem.  2007,  5847 
  • 6f Krishnan KS. Rajan R. Radhakrishnan KV. Synthesis  2008,  1955 
  • 8a Becke AD. J. Chem. Phys.  1993,  98:  5648 
  • 8b Lee CT. Yang WT. Parr RG. Phys. Rev. B  1988,  37:  785 
  • 8c Suresh CH. Ramaiah D. George MV. J. Org. Chem.  2007,  72:  367 
  • 8d Varma L. Ganga VB. Suresh E. Suresh CH. Tetrahedron Lett.  2006,  47:  917 
  • 9 Frisch MJ. Trucks GW. Schlegel HB. Scuseria GE. Robb MA. Cheeseman JR. Montgomery JA. Vreven T. Kudin KN. Burant JC. Millam JM. Iyengar SS. Tomasi J. Barone V. Mennucci B. Cossi M. Scalmani G. Rega N. Petersson GA. Nakatsuji H. Hada M. Ehara M. Toyota K. Fukuda R. Hasegawa J. Ishida M. Nakajima T. Honda Y. Kitao O. Nakai H. Klene M. Li X. Knox JE. Hratchian HP. Cross JB. Adamo C. Jaramillo J. Gomperts R. Stratmann RE. Yazyev O. Austin AJ. Cammi R. Pomelli C. Ochterski JW. Ayala PY. Morokuma K. Voth GA. Salvador P. Dannenberg JJ. Zakrzewski VG. Dapprich S. Daniels AD. Strain MC. Farkas O. Malick DK. Rabuck AD. Raghavachari K. Foresman JB. Ortiz JV. Cui Q. Baboul AG. Clifford S. Cioslowski J. Stefanov BB. Liu G. Liashenko A. Piskorz P. Komaromi I. Martin RL. Fox DJ. Keith T. Al-Laham MA. Peng CY. Nanayakkara A. Challacombe M. Gill PMW. Johnson B. Chen W. Wong MW. Gonzalez C. Pople JA. Gaussian 03, Revision C.02   Gaussian, Inc.; Wallingford CT: 2004. 
  • 10a Gupta S. Das BC. Schafmeister CE. Org. Lett.  2005,  7:  2861 
  • 10b Levins CG. Brown ZZ. Schafmeister CE. Org. Lett.  2006,  8:  2807 
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).