Transannular Hetero Diels-Alder Reaction of Macrocyclic α, β-Unsaturated Thioketones and Synthesis of Oxonin Derivatives by Desulfurization of the Transannular Adducts

Synlett

Volumn 1996, Issue 1, 1996, Pages 72-74

  Moriyama, Satoshi ^a   Karakasa, Takayuki ^b   Inoue, Takashi ^a   Kurashima, Katsumi ^a   Satsumabayashi, Sadayoshi ^b   Saito, Takao ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

^b NIPPON DENTAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002947826     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5330     Document Type: Article

References (20)

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2. Deslongchamps, P. Aldrichimica Acta 1984, 17, 59. Deslongchamps, P. Pure Appl. Chem. 1992, 64, 1831.
3. Takahashi, T.; Shimizu, K.; Doi, T.; Tsuji, J.; Fukazawa, Y. J. Am. Chem. Soc. 1988, 110, 2674. Sakamoto, Y.; Yamada, H.; Takahashi, T. Synlett 1995, 231.
4. Takahashi, T.; Shimizu, K.; Doi, T.; Tsuji, J.; Fukazawa, Y. J. Am. Chem. Soc. 1988, 110, 2674. Sakamoto, Y.; Yamada, H.; Takahashi, T. Synlett 1995, 231.
5. Bérubé, G; Deslongchamps, P. Tetrahedron Lett. 1987, 28, 5255.
6. Karakasa, T.; Motoki, S. J. Org.Chem. 1978, 43, 4147. Karakasa, T.; Motoki, S. J. Org.Chem. 1979, 44, 4151. Motoki, S; Saito, T; Karakasa, T; Matsushita, T.; Furuno, E. J. Chem. Soc., Perkin Trans. 1 1992, 2943.
7. Karakasa, T.; Motoki, S. J. Org.Chem. 1978, 43, 4147. Karakasa, T.; Motoki, S. J. Org.Chem. 1979, 44, 4151. Motoki, S; Saito, T; Karakasa, T; Matsushita, T.; Furuno, E. J. Chem. Soc., Perkin Trans. 1 1992, 2943.
8. Karakasa, T.; Motoki, S. J. Org.Chem. 1978, 43, 4147. Karakasa, T.; Motoki, S. J. Org.Chem. 1979, 44, 4151. Motoki, S; Saito, T; Karakasa, T; Matsushita, T.; Furuno, E. J. Chem. Soc., Perkin Trans. 1 1992, 2943.
9. Saito, T.; Nagashima, M.; Karakasa, T.; Motoki, S. J. Chem. Soc., Chem. Commun. 1990, 1665. Saito, T.; Nagashima, M.; Karakasa, T.; Motoki, S. J. Chem. Soc., Chem. Commun. 1992, 411.
10. Saito, T.; Nagashima, M.; Karakasa, T.; Motoki, S. J. Chem. Soc., Chem. Commun. 1990, 1665. Saito, T.; Nagashima, M.; Karakasa, T.; Motoki, S. J. Chem. Soc., Chem. Commun. 1992, 411.
11. Recently segment synthesis of such medium-membered cyclic ether species directed toward total synthesis of marin toxines (breve toxines) has been reported: Isobe, M.; Yenjai, C.; Tanaka, S. Synlett 1994, 916.
12. 3 in the refluxing acetone for 30 h; 1a: Yield 38 %; pale yellow needles; mp 136-137°C. Similarly 1b was prepared from 1,4-dibromo-2-butene and the sodium salt obtained by aldol condensation of o-vanillin and 2′-hydroxyacetophenone; 1b: Yield 45%; pale yellow cubes; mp 132-134°C.
13. Schraufstätter, E.; Deutsch, S. Chem. Ber. 1948, 81, 489.
14. Ciganek, E. The Intramolecular Diels-Alder Reaction, in Organic Reactions, Vol. 32, New York 1984, p 22.
15. Homing, E. C. Org. Synth., Coll. Vol. III 1955, p 181.
16. LAOCOON III, D. F. Detar, Computer Programs for Chemistry, W. A. Benjamin, Inc., New York 1968, Vol. 1, p 10; Chemistry and Software No. 8007 program was used.
17. The following JCPE (Japan Chemistry Program Exchange) programs were used. a) CONFLEX (program No. P040); b) MOPAC 93 (program No. P081); c) 3JHH2 (program No. P012).
18. It is noteworthy that the unexpectedly small coupling constant between H-1 and H-9 was observed in spite of their traits arrangement, which, however, is consistent with the dihedral angle of 110.6° in the optimized conformer.
19. Burkert, U.; Allinger, N. L. Molecular Mechanics, the American Chemical Society: Washigton, D. C., 1982, chapter 4.
20. Ermer, O.; Lifson, S. J. Am. Chem. Soc. 1973, 95, 4121.