Facile construction of a tricyclo[5.3.0.01,4]decenone ring system by the Brook rearrangement-mediated [3 + 4] annulation

Organic Letters

Volumn 1, Issue 4, 1999, Pages 677-679

  Takeda, Kei ^a   Ohtani, Yasuhiro ^a  

^a UNIVERSITY OF TOYAMA   (Japan)

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EID: 0000675139     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990764n     Document Type: Article

References (15)

1. Takeda, K.; Ohtani, Y.; Ando, E.; Fujimoto, K.; Yoshii, E.; Koizumi, T. Chem. Lett. 1998, 1157-1158.
2. For the [3 + 2] annulation, see: (a) Takeda, K.; Fujisawa, M.; Makino, T.; Yoshii, E.; Yamaguchi, K. J. Am. Chem. Soc. 1993, 115, 9351-9352.
3. (b) Takeda, K.; Nakayama, I.; Yoshii, E. Synlett 1994, 178-178.
4. (c) Takeda, K.; Kitagawa, K.; Nakayama, I.; Yoshii, E. Synlett 1997, 255-256.
5. (a) Takeda, K.; Takeda, M.; Nakajima, A.; Yoshii, E. J. Am. Chem. Soc. 1995, 117, 6400-6401.
6. (b) Takeda, K.; Nakajima, A.; Yoshii, E. Synlert 1996, 753-754.
7. (c) Takeda, K.; Nakajima, A.; Takeda, M.; Okamoto, Y.; Sato, T.; Yoshii, E.; Koizumi, T.; Shiro, M. J. Am. Chem. Soc. 1998, 120, 4947-4959.
8. (d) Takeda, K.; Nakajima, A.; Takeda, M.; Yoshii, E. Org. Synth. 1999, 76, 199-213.
9. (a) Cunico, R. F.; Zhang, C. Tetrahedron Lett. 1992, 33, 6751 -6754.
10. (b) Cunico, R. F.; Zhang, C. Tetrahedron 1995, 51, 9823-9838.
11. -1, and confirmed by a X-ray analysis of 5a after derivatization.
12. -1 which is indicative of the cyclopropyl carbonyl moiety with an siloxyvinyl group, see: Lyle, T. A.; Frei, B. Helv. Chim. Acta 1981, 64, 2598-2605.
13. 1, 4]decenone ring system using α-oxycyclopropylcarbinol-cyclobutanone rearrangement, see: (a) Wenkert, E.; Arrhenius, T. S. J. Am. Chem. Soc. 1983, 105, 2030-2033. For preparation by photochemical reaction, see:
14. (b) Exon, C.; Nobbs, M.; Magnus, P. Tetrahedron 1981, 37, 4515-4519,
15. (c) Wiesner, K. Tetrahedron 1975, 31, 1655-1658, and ref 6.