Asymmetric spirocyclization: A new type of acid-catalyzed intramolecular 1,4-addition to form carba-spirocyclic compounds

Tetrahedron

Volumn 54, Issue 51, 1998, Pages 15555-15566

  Yamada, Satoshi ^a   Karasawa, Satoru ^a   Takahashi, Youichi ^a   Aso, Mariko ^a   Suemune, Hiroshi ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

SPIRO[4.5]DECANE 2,7 DIONE; SPIRO[5.5]UNDECANE 2,8 DIONE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; MOLECULAR INTERACTION; PRIORITY JOURNAL;

EID: 0032542152     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)01009-6     Document Type: Article

References (18)

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2. 1. Suemune, H.; Yoshida, O.; Uchida, J.; Tanaka, M. Tetrahedron Lett., 1995, 36, 7259-7262. Suemune, H.; Uchida, J.; Sakai, K. Heterocycles, 1996, 43, 625-631. And references cited therein.
3. 2. a) For our preliminary communication: Suemune, H.; Takahashi, Y.; Sakai, K. J. Chem. Soc., Chem. Commun. 1993, 1858-1859.
4. b) For amine spirocyclization: Goldeski, S. A.; Heacock, D. J. J. Org. Chem., 1982, 47, 4822-4824. Fukuyama, T.; Avantani, M. J. Org. Chem., 1975, 40, 2011.
5. b) For amine spirocyclization: Goldeski, S. A.; Heacock, D. J. J. Org. Chem., 1982, 47, 4822-4824. Fukuyama, T.; Avantani, M. J. Org. Chem., 1975, 40, 2011.
6. c) For carba-spirocyclization: Danishefsky, S.; Chackalamannil, S., Uang, B.-J.J. Org. Chem., 1982, 47, 2231-2232. Martin, S. F., Desai, S. R. J. Org. Chem., 1977, 42, 1664-1666. Scheffold, R.; Dike, M.; Dike, S.; Herold, T.; Walder, L. J. Am. Chem. Soc., 1980, 102, 3642-3644. Macdonald, T.; Mahalingam, S. J. Am. Chem. Soc., 1980, 102, 2113-2115. Schinzer, D.; Solyom, S.; Becker M. Tetrahedron Lett., 1985, 26, 1831-1834. Kraus, G. A.; Liras, S. Tetrahedron Lett., 1990, 31, 5265-5268.
7. c) For carba-spirocyclization: Danishefsky, S.; Chackalamannil, S., Uang, B.-J.J. Org. Chem., 1982, 47, 2231-2232. Martin, S. F., Desai, S. R. J. Org. Chem., 1977, 42, 1664-1666. Scheffold, R.; Dike, M.; Dike, S.; Herold, T.; Walder, L. J. Am. Chem. Soc., 1980, 102, 3642-3644. Macdonald, T.; Mahalingam, S. J. Am. Chem. Soc., 1980, 102, 2113-2115. Schinzer, D.; Solyom, S.; Becker M. Tetrahedron Lett., 1985, 26, 1831-1834. Kraus, G. A.; Liras, S. Tetrahedron Lett., 1990, 31, 5265-5268.
8. c) For carba-spirocyclization: Danishefsky, S.; Chackalamannil, S., Uang, B.-J.J. Org. Chem., 1982, 47, 2231-2232. Martin, S. F., Desai, S. R. J. Org. Chem., 1977, 42, 1664-1666. Scheffold, R.; Dike, M.; Dike, S.; Herold, T.; Walder, L. J. Am. Chem. Soc., 1980, 102, 3642-3644. Macdonald, T.; Mahalingam, S. J. Am. Chem. Soc., 1980, 102, 2113-2115. Schinzer, D.; Solyom, S.; Becker M. Tetrahedron Lett., 1985, 26, 1831-1834. Kraus, G. A.; Liras, S. Tetrahedron Lett., 1990, 31, 5265-5268.
9. c) For carba-spirocyclization: Danishefsky, S.; Chackalamannil, S., Uang, B.-J.J. Org. Chem., 1982, 47, 2231-2232. Martin, S. F., Desai, S. R. J. Org. Chem., 1977, 42, 1664-1666. Scheffold, R.; Dike, M.; Dike, S.; Herold, T.; Walder, L. J. Am. Chem. Soc., 1980, 102, 3642-3644. Macdonald, T.; Mahalingam, S. J. Am. Chem. Soc., 1980, 102, 2113-2115. Schinzer, D.; Solyom, S.; Becker M. Tetrahedron Lett., 1985, 26, 1831-1834. Kraus, G. A.; Liras, S. Tetrahedron Lett., 1990, 31, 5265-5268.
10. c) For carba-spirocyclization: Danishefsky, S.; Chackalamannil, S., Uang, B.-J.J. Org. Chem., 1982, 47, 2231-2232. Martin, S. F., Desai, S. R. J. Org. Chem., 1977, 42, 1664-1666. Scheffold, R.; Dike, M.; Dike, S.; Herold, T.; Walder, L. J. Am. Chem. Soc., 1980, 102, 3642-3644. Macdonald, T.; Mahalingam, S. J. Am. Chem. Soc., 1980, 102, 2113-2115. Schinzer, D.; Solyom, S.; Becker M. Tetrahedron Lett., 1985, 26, 1831-1834. Kraus, G. A.; Liras, S. Tetrahedron Lett., 1990, 31, 5265-5268.
11. c) For carba-spirocyclization: Danishefsky, S.; Chackalamannil, S., Uang, B.-J.J. Org. Chem., 1982, 47, 2231-2232. Martin, S. F., Desai, S. R. J. Org. Chem., 1977, 42, 1664-1666. Scheffold, R.; Dike, M.; Dike, S.; Herold, T.; Walder, L. J. Am. Chem. Soc., 1980, 102, 3642-3644. Macdonald, T.; Mahalingam, S. J. Am. Chem. Soc., 1980, 102, 2113-2115. Schinzer, D.; Solyom, S.; Becker M. Tetrahedron Lett., 1985, 26, 1831-1834. Kraus, G. A.; Liras, S. Tetrahedron Lett., 1990, 31, 5265-5268.
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18. 2 gave better results for the reproducibility.