PDF herunterladen
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
Weitere Informationen

Publikationsverlauf

Received 31 March 2008
Publikationsdatum:
11. Juni 2008 (online)

    Lizenzen und Reprints Alle Artikel dieser Rubrik

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.

Key words

pentafulvenes - oxidopyrylium betaines - oxa-bridged spirocycles - macromolecules

    References

  • 1a Brito I. Cueto M. Diaz-Marrero AR. Parias J. Martin AS. J. Nat. Prod.  2002,  65:  946 
    Suche in Google Scholar
  • 1b Conroy H. Chakrabarti JK. Tetrahedron  1959,  4:  6 
    Suche in Google Scholar
  • 1c Cui CB. Kakeya H. Osada H. Tetrahedron  1996,  52:  12651 
    Suche in Google Scholar
  • 1d Cui CB. Kakeya H. Osada H. J. Antibiot.  1996,  49:  832 
    Suche in Google Scholar
  • 1e Cui CB. Kakeya H. Osada H. Tetrahedron  1997,  53:  59 
    Suche in Google Scholar
  • 1f Daly JW. Karle I. Myers C. Tokuyama T. Waters JA. Witkop B. Proc. Natl. Acad. Sci. U.S.A.  1971,  68:  1870 
    Suche in Google Scholar
  • 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 
    CrossrefSuche in Google Scholar
  • 2b Goehring RR. Org. Prep. Proced. Int.  1995,  27:  691 
    CrossrefSuche in Google Scholar
  • 2c Edmondson S. Danishefsky SJ. Sepp-Lorenzino I. Rosen N. J. Am. Chem. Soc.  1999,  121:  2147 
    CrossrefSuche in Google Scholar
  • 3a Alper PB. Meyers C. Lerchner A. Siegel DR. Carreira EM. Angew. Chem. Int. Ed.  1999,  38:  3186 
    CrossrefSuche in Google Scholar
  • 3b Trost BM. Yong B. Miller ML. J. Am. Chem. Soc.  1989,  111:  6482 
    CrossrefSuche in Google Scholar
  • 4a Pages L. Llebaria A. Camps F. Molins E. Miravitlles C. Moreto JM. J. Am. Chem. Soc.  1992,  114:  10449 
    CrossrefSuche in Google Scholar
  • 4b Oda M. Fukuta A. Kajioka T. Uchiyama T. Kainuma H. Miyatake R. Kuroda S. Tetrahedron  2000,  56:  9917 
    CrossrefSuche in Google Scholar
  • 5a Anas S. Krishnan KS. Sajisha VS. Anju KS. Radhakrishnan KV. Suresh E. Suresh CH. New J. Chem.  2007,  31:  237 
    CrossrefSuche in Google Scholar
  • 5b Radhakrishnan KV. Anas S. Suresh E. Koga N. Suresh CH. Bull. Chem. Soc. Jpn.  2007,  80:  484 
    CrossrefSuche in Google Scholar
  • 5c Anas S. Sajisha VS. Mohanlal S. Radhakrishnan KV. Synlett  2006,  2399 
    Crossref
  • 5d Nair V. Jayan CN. Radhakrishnan KV. Anilkumar G. Rath NP. Tetrahedron  2001,  57:  5807 
    CrossrefSuche in Google Scholar
  • 6a Radhakrishnan KV. Krishnan KS. Bhadbhade MM. Bhosekar GV. Tetrahedron Lett.  2005,  46:  4785 
    Thieme ConnectSuche in Google Scholar
  • 6b Krishnan KS. Sajisha VS. Anas S. Suresh CH. Bhadbhade MM. Bhosekar GV. Radhakrishnan KV. Tetrahedron  2006,  62:  5952 
    Thieme ConnectSuche in Google Scholar
  • 6c Krishnan KS. Suresh E. Mathew S. Radhakrishnan KV. Synthesis  2006,  1811 
    Thieme Connect
  • 6d Krishnan KS. Smitha M. Suresh E. Radhakrishnan KV. Tetrahedron  2006,  62:  12345 
    Thieme ConnectSuche in Google Scholar
  • 6e Krishnan KS. Kuthanapillil JM. Rajan R. Suresh E. Radhakrishnan KV. Eur. J. Org. Chem.  2007,  5847 
    Thieme Connect
  • 6f Krishnan KS. Rajan R. Radhakrishnan KV. Synthesis  2008,  1955 
    Thieme Connect
  • 8a Becke AD. J. Chem. Phys.  1993,  98:  5648 
    CrossrefSuche in Google Scholar
  • 8b Lee CT. Yang WT. Parr RG. Phys. Rev. B  1988,  37:  785 
    CrossrefSuche in Google Scholar
  • 8c Suresh CH. Ramaiah D. George MV. J. Org. Chem.  2007,  72:  367 
    CrossrefSuche in Google Scholar
  • 8d Varma L. Ganga VB. Suresh E. Suresh CH. Tetrahedron Lett.  2006,  47:  917 
    CrossrefSuche in Google Scholar
  • 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 
    CrossrefSuche in Google Scholar
  • 10b Levins CG. Brown ZZ. Schafmeister CE. Org. Lett.  2006,  8:  2807 
    CrossrefSuche in Google Scholar
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).