Cyclisation vs acylL migration OF α-allyl lactone dreived anion : Synthesis of spiro[4,5]dec-2-ene-1,6-diones

Tetrahedron Letters

Volumn 37, Issue 18, 1996, Pages 3199-3202

  Jaivisuthunza, W ^a   Tarnchompoo, B ^b   Thebtaranonth, C ^b   Thebtaranonth, Y ^a  

^a Mahidol University   (Thailand)

^b NATIONAL SCIENCE AND TECHNOLOGY DEVELOPMENT AGENCY   (Thailand)

Author keywords

[No Author keywords available]

Indexed keywords

GAMMA BUTYROLACTONE DERIVATIVE; SPIRO COMPOUND; SPIRO[4.5]DECANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0029997292     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00494-7     Document Type: Article

References (20)

1. Prempree, P.; Siwapinyoyos, T.; Thebtaranonth, C.; Thebtaranonth, Y. Tetrahedron Lett., 1980, 21, 1169.
2. Siwapinyoyos, T.; Thebtaranonth, Y. J. Org. Chem., 1982, 47, 598. Methylenomycins A and B: isolation and structures; Haneishi, T.; Kitahara, N.; Takiguchi, Y.; Arai, M.; Sugawara, S. J. Antibiot., 1974, 27, 386; Haneishi, T.; Terahara, A.; Arai, M.; Hata, T.; Tamura, C. J. Antibiot., 1974, 27, 393; review up to 1979, Terahara, A.; Haneishi, T.; Arai, M. Heterocycles, 1979, 13, 353.
3. Siwapinyoyos, T.; Thebtaranonth, Y. J. Org. Chem., 1982, 47, 598. Methylenomycins A and B: isolation and structures; Haneishi, T.; Kitahara, N.; Takiguchi, Y.; Arai, M.; Sugawara, S. J. Antibiot., 1974, 27, 386; Haneishi, T.; Terahara, A.; Arai, M.; Hata, T.; Tamura, C. J. Antibiot., 1974, 27, 393; review up to 1979, Terahara, A.; Haneishi, T.; Arai, M. Heterocycles, 1979, 13, 353.
4. Siwapinyoyos, T.; Thebtaranonth, Y. J. Org. Chem., 1982, 47, 598. Methylenomycins A and B: isolation and structures; Haneishi, T.; Kitahara, N.; Takiguchi, Y.; Arai, M.; Sugawara, S. J. Antibiot., 1974, 27, 386; Haneishi, T.; Terahara, A.; Arai, M.; Hata, T.; Tamura, C. J. Antibiot., 1974, 27, 393; review up to 1979, Terahara, A.; Haneishi, T.; Arai, M. Heterocycles, 1979, 13, 353.
5. Siwapinyoyos, T.; Thebtaranonth, Y. J. Org. Chem., 1982, 47, 598. Methylenomycins A and B: isolation and structures; Haneishi, T.; Kitahara, N.; Takiguchi, Y.; Arai, M.; Sugawara, S. J. Antibiot., 1974, 27, 386; Haneishi, T.; Terahara, A.; Arai, M.; Hata, T.; Tamura, C. J. Antibiot., 1974, 27, 393; review up to 1979, Terahara, A.; Haneishi, T.; Arai, M. Heterocycles, 1979, 13, 353.
6. Thebtaranonth, Y. Pure and Applied Chem., 1986, 58, 781.
7. Mahidol, C.; Thebtaranonth, C.; Thebtaranonth, Y.; Yenjai, C. Tetrahedron Lett., 1989, 30, 3857. Deepoxy-4,5-didehydromethylenomycin A: isolation and structure; Hornemann, U.; Hopwood, D. A. Tetrahedron Lett., 1978, 2977.
8. Mahidol, C.; Thebtaranonth, C.; Thebtaranonth, Y.; Yenjai, C. Tetrahedron Lett., 1989, 30, 3857. Deepoxy-4,5-didehydromethylenomycin A: isolation and structure; Hornemann, U.; Hopwood, D. A. Tetrahedron Lett., 1978, 2977.
9. Kodpinid, M.; Siwapinyoyos, T.; Thebtaranonth, Y. J. Am. Chem. Soc., 1984, 106, 4862. Sarkomycin: isolation and structure; Umezawa, H.; Takeuchi, T.; Nitta, K.; Yamamoto, Y.; Yamaoka, S. J. Antibiot., 1953, 6, 153; see also, Scarborough, Jr., R. M.; Toder, B. H.; Smith, III, A. B. J. Am. Chem. Soc., 1980, 102, 3904.
10. Kodpinid, M.; Siwapinyoyos, T.; Thebtaranonth, Y. J. Am. Chem. Soc., 1984, 106, 4862. Sarkomycin: isolation and structure; Umezawa, H.; Takeuchi, T.; Nitta, K.; Yamamoto, Y.; Yamaoka, S. J. Antibiot., 1953, 6, 153; see also, Scarborough, Jr., R. M.; Toder, B. H.; Smith, III, A. B. J. Am. Chem. Soc., 1980, 102, 3904.
11. Kodpinid, M.; Siwapinyoyos, T.; Thebtaranonth, Y. J. Am. Chem. Soc., 1984, 106, 4862. Sarkomycin: isolation and structure; Umezawa, H.; Takeuchi, T.; Nitta, K.; Yamamoto, Y.; Yamaoka, S. J. Antibiot., 1953, 6, 153; see also, Scarborough, Jr., R. M.; Toder, B. H.; Smith, III, A. B. J. Am. Chem. Soc., 1980, 102, 3904.
12. Mahidol, C.; Pinyopronpanit, Y.; Radviroongit, S.; Thebtaranonth, C.; Thebtaranonth, Y. J. Chem. Soc., Chem. Commun., 1988, 1382.
13. All yields reported are isolated yields and all compounds described give satisfactory spectroscopic as well as elemental analysis data. Compounds 7 and 13 are obtained as mixtures of about equal amounts of two (separable) diastereoisomers.
14. Sato, M.; Ogasawara, H.; Oi, K.; Kato, T. Chem. Pharm. Bull., 1983, 31, 1896; Kaneko, C.; Sato, M.; Sakaki, J.; Abe, Y. J. Heterocyclic Chem., 1990, 27, 25; see also, Winkler, J.D.; Bowen, C. M.; Liotta, F. Chem. Rev., 1995, 95, 2003.
15. Sato, M.; Ogasawara, H.; Oi, K.; Kato, T. Chem. Pharm. Bull., 1983, 31, 1896; Kaneko, C.; Sato, M.; Sakaki, J.; Abe, Y. J. Heterocyclic Chem., 1990, 27, 25; see also, Winkler, J.D.; Bowen, C. M.; Liotta, F. Chem. Rev., 1995, 95, 2003.
16. Sato, M.; Ogasawara, H.; Oi, K.; Kato, T. Chem. Pharm. Bull., 1983, 31, 1896; Kaneko, C.; Sato, M.; Sakaki, J.; Abe, Y. J. Heterocyclic Chem., 1990, 27, 25; see also, Winkler, J.D.; Bowen, C. M.; Liotta, F. Chem. Rev., 1995, 95, 2003.
17. Bach, R. D.; Tubergen, M. W.; Klix, R. C. Tetrahedron Lett., 1986, 27, 3565; Hayashi, T.; Kanehira, K.; Hagihara, T.; Kumada, M. J. Org. Chem., 1988, 53, 113; Kirmse, W.; Söllenböhmer, F. J. Am. Chem. Soc., 1989, 111, 4127; Chitkul, B.; Pinyopronpanich, Y.; Thebtaranonth, C.; Thebtaranonth, Y.; Taylor, W. C. Tetrahedron Lett., 1994, 35, 1099.
18. Bach, R. D.; Tubergen, M. W.; Klix, R. C. Tetrahedron Lett., 1986, 27, 3565; Hayashi, T.; Kanehira, K.; Hagihara, T.; Kumada, M. J. Org. Chem., 1988, 53, 113; Kirmse, W.; Söllenböhmer, F. J. Am. Chem. Soc., 1989, 111, 4127; Chitkul, B.; Pinyopronpanich, Y.; Thebtaranonth, C.; Thebtaranonth, Y.; Taylor, W. C. Tetrahedron Lett., 1994, 35, 1099.
19. Bach, R. D.; Tubergen, M. W.; Klix, R. C. Tetrahedron Lett., 1986, 27, 3565; Hayashi, T.; Kanehira, K.; Hagihara, T.; Kumada, M. J. Org. Chem., 1988, 53, 113; Kirmse, W.; Söllenböhmer, F. J. Am. Chem. Soc., 1989, 111, 4127; Chitkul, B.; Pinyopronpanich, Y.; Thebtaranonth, C.; Thebtaranonth, Y.; Taylor, W. C. Tetrahedron Lett., 1994, 35, 1099.
20. Bach, R. D.; Tubergen, M. W.; Klix, R. C. Tetrahedron Lett., 1986, 27, 3565; Hayashi, T.; Kanehira, K.; Hagihara, T.; Kumada, M. J. Org. Chem., 1988, 53, 113; Kirmse, W.; Söllenböhmer, F. J. Am. Chem. Soc., 1989, 111, 4127; Chitkul, B.; Pinyopronpanich, Y.; Thebtaranonth, C.; Thebtaranonth, Y.; Taylor, W. C. Tetrahedron Lett., 1994, 35, 1099.