Lituarine synthetic studies. An efficient, stereocontrolled construction of the common C(7-19) tricyclic spiroketal fragment

Organic Letters

Volumn 3, Issue 24, 2001, Pages 3979-3982

  Smith III, Amos B ^a   Frohn, Michael ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EPOXIDE; LITUARINE A; LITUARINE B; LITUARINE C; SPIRO COMPOUND;

ARTICLE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

EPOXY COMPOUNDS; SPIRO COMPOUNDS; STEREOISOMERISM; SUPPORT, NON-U.S. GOV'T; SUPPORT, U.S. GOV'T, P.H.S.;

EID: 0035969590     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016948v     Document Type: Article

References (31)

1. Vidal, J.-P.; Escale, R.; Girard, J.-P.; Rossi, J.-C.; Chantraine, J.-M.; Aumelas, A. J. Org. Chem. 1992, 57, 5857-5860.
2. Okadaic acid contains a similar tricyclic fragment but is devoid of the methyl substituents at C(12) and C(16), see: Tachibana, K.; Scheuer, P. J.; Tsukitani, Y.; Kikuchi, H.; Engen, D. V.; Clardy, J.; Gopichand, Y.; Schmitz, F. J. J. Am. Chem. Soc. 1981, 103, 2469-2471.
3. For the construction of dienamides, see: (a) Oppolzer, W.; Frostl, W. Helv. Chim. Acta 1975, 58, 587-589.
4. (b) Overman, L. E.; Clizbe, L. A. J. Am. Chem. Soc. 1976, 98, 2352-2354.
5. (c) Overman, L. E.; Taylor, G. F.; Jessup, P. J. Tetrahedron Lett. 1976, 3089-3092.
6. (d) Katritzky, A. R.; Ignatchenko, A. V.; Lang, H.; J. Org. Chem. 1995, 60, 4002-4005.
7. (a) Smith, A. B., III; Hale, K. J.; Vaccaro, H. A.; Rivero, R. A. J. Am. Chem. Soc. 1991, 113, 2112-2122
8. (b) Smith, A. B., III; Friestad, G. K.; Barbosa, J.; Bertounesque, E.; Hull, K. G.; Iwashima, M.; Qiu, Y.; Salvatore, B. A.; Spoors, P. G.; Duan, J. J.-W. J. Am. Chem. Soc. 1999, 121, 10468-10477.
9. (c) Smith, A. B., III; Doughty, V. A.; Lin, Q.; Zhuang, L.; McBriar, M. D.; Boldi, A. M.; Moser, W. H.; Murase, N.; Nakayama, K.; Sobukawa, M. Angew. Chem., Int. Ed. Engl. 2001, 40. 191-195.
10. (d) Smith, A. B.. III; Lin, Q.; Doughty, V. A.; Zhuang, L.; McBriar, M. D.; Kerns, J. K.; Brook, C. S.; Murase, N.; Nakayama, K. Angew. Chem., Int. Ed. Engl. 2001, 40, 196-199.
11. For other methods for the construction of the fused tetrahydropyrans, see: (a) Rainier, J. D.; Allwein, S. P.; Cox, J. M. J. Org. Chem. 2001, 66, 1380-1386 and references therein.
12. (b) Sakamoto, Y.; Matsuo, G.; Matsukura, H.; Nakata, T. Org. Lett. 2001, 3, 2749-2752.
13. In general, 5-exo cyclization is favored geometrically over 6-endo cyclization. Baldwin, J. E. J. Chem. Soc., Chem. Commun. 1976, 734-736.
14. (a) Nicolaou, K. C.; Duggan, M. E.; Hwang, C.-K.; Somers, P. K. J. Chem Soc., Chem. Commun. 1985, 1359-1362.
15. (b) Nicolaou, K. C.; Prasad, C. V. C.; Somers, P. K.; Hwang, C.-K. J. Am. Chem. Soc. 1989, 111, 5330-5334.
16. For reviews of the anomeric effect, see: (a) Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry; Pergamon Press: New York, 1983.
17. (b) Kirby, A. J. The Anomeric Effect and Related Stereoelectronic Effects at Oxygen; Springer-Verlag: New York, 1983.
18. Monte Carlo conformational searches using the MM2 force field predicted the spiroketal epimeric to 4 at C(16) (i.e., β) to be more stable by 0.99 kcal/mol (1.49:1 ratio at equilibrium). Both methyl isomers epimeric at C(15) were predicted to be considerably less stable (ca. 7.7 kcal/mol).
19. Smith, A. B., III; Zhuang, L.; Brook, C. S.; Boldi, A. M.; McBriar, M. D.; Moser, W. H.; Murase, N.; Nakayama, K.; Verhoest, P. R.; Lin, Q. Tetrahedron Lett. 1997, 38, 8667-8670.
20. Interestingly, minor amounts (<10%) of regioisomeric products were also observed.
21. Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765-5780.
22. Omura, K.; Swern, D. Tetrahedron 1978, 34, 1651-1660.
23. Furrow, M. E.; Schaus S. E.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 6776-6777.
24. (a) Myers, A. G.; McKinstry, L. J. Org. Chem. 1996, 61, 2428-2440.
25. (b) Myers, A. G.; Yang, B. H. Org. Synth. 1999, 47, 22-28.
26. Ditrich, K.; Hoffmann, R. W. Tetrahedron Lett. 1985, 26, 6325-6328.
27. Ley, S. V.; Meek, G. J. Chem. Soc., Perkin Trans. 1 1997, 1125-1133.
28. A mixture (ca. 1:1) of 6-endo/5-exo products was obtained in poor yield.
29. (19l Gemal, A. L.; Luche, J.-L. J. Am. Chem. Soc. 1981, 103, 5454-5459.
30. Keinan, E.; Gleize, P. A. Tetrahedron Lett. 1982, 23, 477-480.
31. 13C, DEPT; 2D COSY, NOESY, HMQC, and HMBC NMR.