Diastereoselective synthesis of the trans-anti-cis-decahydro-as-indacene ring system via the transannular Diels-Alder reaction of a functionalized (E,E,E)-cyclododeca-1,6,8-triene

Tetrahedron Letters

Volumn 37, Issue 45, 1996, Pages 8065-8068

  Roush, William R ^a   Works, Andrea B ^a  

^a INDIANA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

INDAN DERIVATIVE; MACROCYCLIC COMPOUND; POLYCYCLIC HYDROCARBON;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

BETULACEAE;

EID: 0030569339     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01840-0     Document Type: Article

References (31)

1. (1) Ito, S.; Hirata, Y. Bull. Chem. Soc. Jpn. 1977, 50, 1813, and references cited therein.
2. (2) Martynow, J. G.; Kirst, H. A. J. Org. Chem. 1994, 59, 1548 and references cited therein.
3. (3) Paquette, L. A.; Macdonald, D.; Anderson, L. G. J. Am. Chem. Soc. 1990, 112, 9292, and references cited therein.
4. (4) Boeckman, R. K., Jr.; Weidner, C. H.; Perni, R. B.; Napier, J. J. J. Am. Chem. Soc. 1989, 111, 8036.
5. (5) Roush, W. R.; Wada, C. K. J. Am. Chem. Soc. 1994, 116, 2151 (a formal total synthesis).
6. (6) Evans, D. A.; Black, W. C. J. Am. Chem. Soc. 1993, 115, 4497.
7. (7) Boeckman, R. K., Jr.; Napier, J. J.; Thomas, E. W.; Sato, R. I. J. Org. Chem. 1983, 48, 4152.
8. (8) Roush, W. R. In Comprehensive Organic Synthesis; B. M. Trost, Ed.; Pergamon Press: Oxford, 1991; Vol. 5; pp 513-550.
9. (9) Deslongchamps, P. Aldrichimica Acta 1991, 24, 43.
10. (10) Roush, W. R.; Warmus, J. S.; Works, A. B. Tetrahedron Lett. 1993, 34, 4427.
11. (11) Works, A. B. Ph. D. Thesis, Indiana University, 1995.
12. (12) Jung, S. H.; Lee, Y. S.; Park, H.; Kwon, D.-S. Tetrahedron Lett. 1995, 36, 1051.
13. (13) Warmus, J. S. Ph. D. Thesis, Massachusetts Institute of Technology, 1990.
14. (14) Bérubé, G.; Deslongchamps, P. Tetrahedron Lett. 1987, 28, 5255.
15. (15) Funk, R. L.; Abelman, M. M.; Munger, J. D., Jr. Tetrahedron 1986, 42, 2831.
16. (16) Cameron, A. G.; Knight, D. W. J. Chem. Soc., Perkin 1 1986, 161.
17. (17) Wipf, P. In Comprehensive Organic Synthesis; B. M. Trost, Ed.; Pergamon Press: Oxford, 1991; Vol. 5; pp 827-873.
18. (18) Funk, R. L.; Olmstead, T. A.; Parvez, M.; Stallman, J. B. J. Org. Chem. 1993, 58, 5873, and literature cited therein.
19. (19) Schreiber, S. L.; Claus, R. E.; Reagan, J. E. Tetrahedron Lett. 1982, 23, 3867.
20. 13C NMR, IR and high resolution mass spectroscopy. Satisfactory C, H combustion analytical data were obtained for intermediates 8 and 10-16.
21. (21) Fatiadi, A. J. Synthesis 1987, 85.
22. (22) Grée, R. Synthesis 1989, 341.
23. 3 complexes, see: Roush, W. R.; Works, A. B. Tetrahedron Lett., manuscript in preparation.
24. 3 unit proceeded in less than 20% yield.
25. (25) Still, W. C.; Gennari, C. Tetrahedron Lett. 1983, 24, 4405.
26. (26) Kunz, H.; Waldmann, H. Angew. Chem., Int. Ed. Engl. 1984, 23, 71.
27. (27) Meng, Q.; Hesse, M. Topics Curr. Chem. 1991, 161, 107-176.
28. (28) Frérot, E.; Coste, J.; Pantaloni, A.; Dufour, M.-N.; Jouin, P. Tetrahedron 1991, 47, 259.
29. (29) Tone, H.; Nishi, T.; Oikawa, Y.; Hikota, M.; Yonemitsu, O. Tetrahedron Lett. 1987, 28, 4569.
30. (30) The stereochemistry and hence the origin of the minor diastereomer has not been determined.
31. (31) We thank Dr. John Huffman for the X-ray structure determination of 5 (Indiana University Molecular Structure Center Report No. 95180).