Enantiospecific approach to a quinane skeleton related to pentalenolactones

Tetrahedron Letters

Volumn 38, Issue 50, 1997, Pages 8623-8626

  Pellegrinet, Silvina C ^a   Spanevello, Rolando A ^a  

^a Universidad Nacional de Rosario   (Argentina)

Author keywords

[No Author keywords available]

Indexed keywords

PENTALENOLACTONE; SESQUITERPENE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

BETULACEAE;

EID: 0030816869     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10370-7     Document Type: Article

References (19)

1. Martin, D. G.; Slomp, G.; Mizsak, S.; Duchamp, D. J.; Chidester, C. G. Tetrahedron Lett. 1970, 4901.
2. For pentalenolactone A to P see: Cane, D. E.; Sohng, J. K.; Williard, P. G. J. Org. Chem. 1992, 57, 844 and references therein cited.
3. Nakagawa, A.; Tomoda, H.; Hao, M. V.; Okano, K.; Iwai, Y.; Omura, S. J. Antibiot. 1985, 38, 111.
4. For enzyme inhibitions studies see: a.-Duszenko, M.; Mecke, D. Mol. Biochem. Parasitol. 1986, 19, 223;
5. b.-Cane, D. E.; Sohng, J. K. Arch. Biochem. Byophys. 1989, 270, 50;
6. c.-Fröhlich, K. U.; Wiedmann, M.; Lottspeich, F.; Mecke, D. J. Antibiot. 1989, 171, 6696;
7. d.-Lambeir, A. M.; Loiseau, A. M.; Kuntz, D. A.; Vellieux, F. M.; Michels, P. A. M.; Opperdoes, F. R. Eur. J. Biochem. 1991, 198, 429;
8. e.-Willson, M.; Lauth, N.; Perie, J.; Callens, M.; Opperdoes, F. R. Biochem. 1994, 33, 214;
9. f.-Cane, D. E.; Sohng, J. K. Biochem. 1994, 33, 6524.
10. First total synthesis of (±) pentalenolactone: Danishefsky, S.; Hirama, M.; Gombatz, K.; Harayama, T.; Berman, E.; Schuda, P. J. Am. Chem. Soc. 1978, 100, 6536.
11. Mori, K.; Tsuji, M. Tetrahedron Lett. 1988, 44, 2835.
12. For a recent review on the syntheses of polyquinanes including the pentalenolactones see: Mehta, G.; Srikrishna, A. Chem. Rev. 1997, 97, 671 and references therein cited.
13. Spanevello, R. A.; Pellegrinet, S. C. Synth. Comm. 1995, 25, 3663.
14. Pellegrinet, S. C.; Spanevello, R. A. Tetrahedron: Asymmetry 1997, 8, 1983.
15. Luche, J. L.; Damiano, J. C. J. Am. Chem. Soc. 1980, 102, 7927.
16. Baldwin, J. Chem. Commun. 1976, 734.
17. The numbering used for pentalenolactone corresponds to the one given in references 1 and 2.
18. 13C NMR spectra. HRMS confirmed the structure of compounds 5, 6b, 7, 9 and satisfactory elemental analysis were obtained for compounds 5, 6a, 9 and 11.
19. 7: C= 66.65, H= 6.32, O= 27.02. Found: C= 66.50, H= 6.40