Facile Synthesis of the Tricyclic Core of Sarain A. 3-Oxidopyridinium Betaine Cycloaddition Approach

Organic Letters

Volumn 1, Issue 12, 1999, Pages 2017-2019

  Sung, Moo Je ^a   Lee, Hyoung Ik ^a   Chong, Youhoon ^a   Cha, Jin Kun ^a  

^a UNIVERSITY OF ALABAMA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3 OXIDOPYRIDINIUM BETAINE; 3-OXIDOPYRIDINIUM BETAINE; BETAINE; BRIDGED COMPOUND; PYRIDINIUM DERIVATIVE; SARAIN A;

ANIMAL; ARTICLE; CHEMISTRY; CYCLIZATION; OXIDATION REDUCTION REACTION; SPONGE (PORIFERA); SYNTHESIS;

ANIMALS; BETAINE; BRIDGED COMPOUNDS; CYCLIZATION; OXIDATION-REDUCTION; PORIFERA; PYRIDINIUM COMPOUNDS;

EID: 0033576423     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9911932     Document Type: Article

References (26)

1. Part 11 in the series of synthetic studies on [4 + 3] cycloadditions of oxyallyls. See the following. (a) Part 10: Lee, K.; Cha, J. K. Org. Lett. 1999, 1, 523
2. (b) Part 9: Cho, S. Y.; Lee, J. C.; Cha, J. K. J. Org. Chem. 1999, 64, 3394.
3. (c) Part 8: Lee, J. C.; Jin, S.-j.; Cha, J. K. J. Org. Chem. 1998, 63, 2804.
4. (d) Part 7: Cha, J. K.; Oh, J. Curr. Org. Chem. 1998, 2, 217.
5. (e) Part 6: Jin, S.-j.; Choi, J.-R.; Oh, J.; Lee, D.; Cha, J. K. J. Am. Chem. Soc. 1995, 117, 10914.
6. (a) Cimino, G.; Mattia, C. A.; Mazzarella, L.; Puliti, R.; Scognamiglio, G.; Spinella, A.; Trivellone, E. Tetrahedron 1989, 45, 3863.
7. (b) Guo, Y.; Madaio, A.; Trivellone, E.; Scognamiglio, G.; Cimino, G. Tetrahedron 1996, 52, 8341.
8. (c) Caprioli, V.; Cimino, G.; De Guilio, A.; Madaio, A.; Scognamiglio, G.; Trivellone, E. Comp. Biochem. Physiol. 1992, 103B, 293.
9. Matzanke, N.; Gregg, R. J.; Weinreb, S. M. Org. Prep. Proced. Int. 1998, 30, 1.
10. (a) Sisko, J.; Weinreb, S. M. J. Org. Chem. 1991, 56, 3210.
11. (b) Sisko, J.; Henry, J. R.; Weinreb, S. M. J. Org. Chem. 1993, 58, 4945.
12. (c) Irie, O.; Samizu, K.; Henry, J. R.; Weinreb, S. M. J. Org. Chem. 1999, 64, 587.
13. (a) Henke, B. R.; Kouklis, A. J.; Heathcock, C. H. J. Org. Chem. 1992, 57, 7056.
14. (b) Heathcock, C. H.; Clasby, M.; Griffith, D. A.; Henke, B. R.; Sharp, M. J. Synlett 1995, 467.
15. (c) Denhart, D. J.; Griffith, D. A.; Heathcock, C. H. J. Org. Chem. 1998, 63, 9616.
16. Downham, R.; Ng, F. W.; Overman, L. E. J. Org. Chem. 1998, 63, 8096.
17. Cf. (a) Lathbury, D.; Gallagher, T. J. Chem. Soc., Chem. Commun. 1986, 114.
18. (b) Ha, J. D.; Lee, D.; Cha, J. K. J. Org. Chem. 1997, 62, 4550 and references therein.
19. (a) Dennis, N.; Ibrahim, B.; Katritzky, A. R. J. Chem. Soc., Perkin Trans. 1 1976, 2307. For reviews, see:
20. (b) Dennis, N.; Katritzky, A. R.; Takeuchi, Y. Angew. Chem., Int. Ed. Engl. 1976, 15, 1.
21. (c) Katritzky, A. R.; Dennis, N. Chem. Rev. 1989, 89, 827.
22. By slow addition (via syringe pump) of triethylamine into a mixture of 7 and cyclopentadiene at room temperature, [2π + 4π] endo cycloadduct 8 was obtained in 58% yield, in addition to [4π + 2π] cycloadduct 9 (27%) and [2π + 4π] exo cycloadduct 10 (3.5%). We decided to defer the ultimate regiocontrol to later study.
23. For convenience, the cyclohexane ring in these bicyclic compounds is drawn in the chair conformation. However, the boat conformer is expected to be most stable, in which the two alkyl groups are equatorial.
24. Ley, S. V.; Norman, J.; Griffith, W. P..; Marsden, S. P. Synthesis 1994, 639.
25. (a) Elucidation of the origin of the observed regiocontrol in TPAP oxidation must await further study. (b) Thus, the alternative regioisomer of 14 was unequivocally excluded as the TPAP oxidation product of 13.
26. Lipton, M. F.; Basha, A.; Weinreb, S. M. Organic Syntheses; Wiley: New York, 1988; Collect. Vol. VI, p 492.