An Efficient Stereocontrolled Synthesis of (-)-Stypoldione

Synlett

Volumn 1996, Issue 9, 1996, Pages 913-915

  Abad, Antonio ^a   Agulló, Consuelo ^a   Arnó, Manuel ^a   Cuñat, Ana C ^a   Meseguer, Benjamín ^a   Zaragozá, Ramón J ^a  

^a UNIVERSITY OF VALENCIA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002127432     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5601     Document Type: Article

References (20)

1. (a) Gerwick, W. H.; Fenical W.; Fritsch, N.; Clardy, J. Tetrahedron Lett. 1979, 145.
2. (b) Gerwick, W. H.; Fenical W. J. Org. Chem. 1981, 46, 22; Gerwich, W. H.; Whatley, G. J. Chem. Ecol. 1989, 15, 677.
3. (b) Gerwick, W. H.; Fenical W. J. Org. Chem. 1981, 46, 22; Gerwich, W. H.; Whatley, G. J. Chem. Ecol. 1989, 15, 677.
4. Sun, H. H.; Fenical, W. Tetrahedron Lett. 1979, 685.
5. (a) White, S. J.; Jacobs, R. S. Mol. Pharmacol. 1983, 24, 500.
6. (b) O'Brien, E. T.; Asai, D. J.; Jacobs, R. S.; Wilson, L Mol. Pharmacol. 1989, 35, 635.
7. (a) Falck, J. R.; Chandrasekhar, S.; Manna, S.; Chiu, C.-C. S. J. Am. Chem Soc. 1993, 115, 11606.
8. (b) Mori, K.; Koga, Y. Liebigs Ann. 1995, 1755. For unsuccessful attempts to synthesise 3 see references cited in the later.
9. Abad, A.; Agulló, C.; Arnó, M.; Cuñat, A. C.; Meseguer, B.; Zaragozá, R. J. Synlett, 1994, 733.
10. Cory, R. M.; Renneboog, R. M. J. Org. Chem. 1984, 49, 3898.
11. Larson, G. L.; Klesse, R. J. Org. Chem. 1985, 50, 3627,
12. Gesson, J. P.; Jacquesy, J. C.; Renoux, B. Tetrahedron, 1989, 45, 5853.
13. Corbel, B.; Medinger, L.; Haelters, J. P.; Sturtz, G. Synthesis 1985, 1048.
14. The stereochemistry of the IMDA product was assigned on the basis of reaction mechanism and spectral analysis. This was confirmed by NOE experiments effected on the diketone formed after hydrolysis of the tert-butyldimethylsilyloxy moiety of 10. In particular, irradiation of the Me-10β signal (diterpene numbering) of the hydrolysed product at δ 1.16 ppm gave NOE enhancements for H-2β at 2.42 ppm, H-4β at 2.28 ppm, H-11β 2.32 ppm and Me-8β at 1.06 ppm.
15. Yamashita, M.; Tanaka, Y.; Arita, A.; Nishida, M. J. Org. Chem. 1994, 59, 3500.
16. 3P, THF, rt). See, Spino, C.; Liu, G.; Tu, N.; Girard, S. J. Org. Chem. 1994, 59, 5596 and Cram, D. J.; Grandpre, M.; Knoble, C. B.; Trueblood, K. N. J. Am. Chem. Soc. 1984, 106, 3286.
17. 3P, THF, rt). See, Spino, C.; Liu, G.; Tu, N.; Girard, S. J. Org. Chem. 1994, 59, 5596 and Cram, D. J.; Grandpre, M.; Knoble, C. B.; Trueblood, K. N. J. Am. Chem. Soc. 1984, 106, 3286.
18. Burkow, I. C., Sydnes, L. K.; Ubeda, D. C. N.; Acta Chem. Scand., Ser. B, 1987, 41, 235.
19. 13C NMR spectroscopic data which were superposable on all the signal associated with the CDE rings portions of the corresponding natural products stypoldiol (1) and epistypoldiol.
20. +) calcd 410.2821, obsd 410.2827.