Novel lactonization induced by the phenonium ion

Tetrahedron Letters

Volumn 38, Issue 16, 1997, Pages 2849-2852

  Nagumo, Shinji ^a   Furukawa, Tsuneo ^b   Ono, Machiko ^b   Akita, Hiroyuki ^b  

^a HOKKAIDO INSTITUTE OF TECHNOLOGY   (Japan)

^b TOHO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

GAMMA LACTONE DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031006430     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00479-6     Document Type: Article

References (25)

1. Cram, D. J. J. Am. Chem. Soc. 1949, 71, 3863-3870.; Cram, D. J.; Davis, R. J. Am. Chem. Soc. 1949, 71, 3871-3875.; Cram, D. J. J. Am. Chem. Soc. 1949, 71, 3875-3883.; Cram, D. J. J. Am. Chem. Soc. 1964, 86, 3767-3772.
2. Cram, D. J. J. Am. Chem. Soc. 1949, 71, 3863-3870.; Cram, D. J.; Davis, R. J. Am. Chem. Soc. 1949, 71, 3871-3875.; Cram, D. J. J. Am. Chem. Soc. 1949, 71, 3875-3883.; Cram, D. J. J. Am. Chem. Soc. 1964, 86, 3767-3772.
3. Cram, D. J. J. Am. Chem. Soc. 1949, 71, 3863-3870.; Cram, D. J.; Davis, R. J. Am. Chem. Soc. 1949, 71, 3871-3875.; Cram, D. J. J. Am. Chem. Soc. 1949, 71, 3875-3883.; Cram, D. J. J. Am. Chem. Soc. 1964, 86, 3767-3772.
4. Cram, D. J. J. Am. Chem. Soc. 1949, 71, 3863-3870.; Cram, D. J.; Davis, R. J. Am. Chem. Soc. 1949, 71, 3871-3875.; Cram, D. J. J. Am. Chem. Soc. 1949, 71, 3875-3883.; Cram, D. J. J. Am. Chem. Soc. 1964, 86, 3767-3772.
5. Olah, G. A.; Porter,R. D. J. Am. Chem. Soc. 1971, 93, 6877-6887.; Olah, G. A.; Spear, R. J.; Forsyth, D. A. J. Am. Chem. Soc. 1976, 98, 6284-6289.; Olah, G. A.; Spear, R. J.; Forsyth, D. A. J. Am. Chem. Soc. 1977, 99, 2615-2621.; Fornarini, S.; Muraglia, V. J. Am. Chem. Soc. 1989, 111, 873-877.
6. Olah, G. A.; Porter,R. D. J. Am. Chem. Soc. 1971, 93, 6877-6887.; Olah, G. A.; Spear, R. J.; Forsyth, D. A. J. Am. Chem. Soc. 1976, 98, 6284-6289.; Olah, G. A.; Spear, R. J.; Forsyth, D. A. J. Am. Chem. Soc. 1977, 99, 2615-2621.; Fornarini, S.; Muraglia, V. J. Am. Chem. Soc. 1989, 111, 873-877.
7. Olah, G. A.; Porter,R. D. J. Am. Chem. Soc. 1971, 93, 6877-6887.; Olah, G. A.; Spear, R. J.; Forsyth, D. A. J. Am. Chem. Soc. 1976, 98, 6284-6289.; Olah, G. A.; Spear, R. J.; Forsyth, D. A. J. Am. Chem. Soc. 1977, 99, 2615-2621.; Fornarini, S.; Muraglia, V. J. Am. Chem. Soc. 1989, 111, 873-877.
8. Olah, G. A.; Porter,R. D. J. Am. Chem. Soc. 1971, 93, 6877-6887.; Olah, G. A.; Spear, R. J.; Forsyth, D. A. J. Am. Chem. Soc. 1976, 98, 6284-6289.; Olah, G. A.; Spear, R. J.; Forsyth, D. A. J. Am. Chem. Soc. 1977, 99, 2615-2621.; Fornarini, S.; Muraglia, V. J. Am. Chem. Soc. 1989, 111, 873-877.
9. Hehre, W. J. J. Am. Chem. Soc. 1972, 94, 5919-5920.; Loupy, A.; Ancian, B. Tetrahedron Lett. 1975, 951-954.; Yamabe, S.; Tanaka, T. Nippon Kagaku Kaishi 1986, 1388-1394.
10. Hehre, W. J. J. Am. Chem. Soc. 1972, 94, 5919-5920.; Loupy, A.; Ancian, B. Tetrahedron Lett. 1975, 951-954.; Yamabe, S.; Tanaka, T. Nippon Kagaku Kaishi 1986, 1388-1394.
11. Hehre, W. J. J. Am. Chem. Soc. 1972, 94, 5919-5920.; Loupy, A.; Ancian, B. Tetrahedron Lett. 1975, 951-954.; Yamabe, S.; Tanaka, T. Nippon Kagaku Kaishi 1986, 1388-1394.
12. (a) For MeOH: Fornarini, S.; Sparapani, C.; Speranza, M. J. Am. Chem. Soc., 1988, 110, 34-41.; Fornarini, S.; Sparapani, C.; Speranza, M. J. Am. Chem. Soc., 1988, 110, 42-46.
13. (a) For MeOH: Fornarini, S.; Sparapani, C.; Speranza, M. J. Am. Chem. Soc., 1988, 110, 34-41.; Fornarini, S.; Sparapani, C.; Speranza, M. J. Am. Chem. Soc., 1988, 110, 42-46.
14. (b) For halogen anion: Fain, D.; Dubois, J.-E.; J. Org. Chem., 1987, 52, 260-267.
15. (c) For Friedel-Crafts alkylation: Matsuda, S.; Nakajima, T.; Suga, S. Bull. Chem. Soc. Jpn. 1983, 56, 1089-1094.
16. (d) For carboxylate: ref 1.
17. We have already developed two methods for conversion of 1 into 2a-j: (a) Friedel-Crafts type reaction; Ono, M.; Yamamoto, Y.; Todoriki, R.; Akita, H. Heterocycles 1994, 37, 181-185.; Ono, M.; Todoriki, R.; Yamamoto, Y.; Akita, H. Chem. Pharm. Bull. 1994, 42, 1590-1595.; Ono, M.; Yamamoto, Y.; Akita, H. Chem. Pham. Bull. 1995, 43, 553-558.
18. We have already developed two methods for conversion of 1 into 2a-j: (a) Friedel-Crafts type reaction; Ono, M.; Yamamoto, Y.; Todoriki, R.; Akita, H. Heterocycles 1994, 37, 181-185.; Ono, M.; Todoriki, R.; Yamamoto, Y.; Akita, H. Chem. Pharm. Bull. 1994, 42, 1590-1595.; Ono, M.; Yamamoto, Y.; Akita, H. Chem. Pham. Bull. 1995, 43, 553-558.
19. We have already developed two methods for conversion of 1 into 2a-j: (a) Friedel-Crafts type reaction; Ono, M.; Yamamoto, Y.; Todoriki, R.; Akita, H. Heterocycles 1994, 37, 181-185.; Ono, M.; Todoriki, R.; Yamamoto, Y.; Akita, H. Chem. Pharm. Bull. 1994, 42, 1590-1595.; Ono, M.; Yamamoto, Y.; Akita, H. Chem. Pham. Bull. 1995, 43, 553-558.
20. (b) Coupling reaction by copper reagent; Nagumo, S.; Irie, S.; Akita, H. J. Chem. Soc., Chem. Commun. 1995, 2001-2002.; Nagumo, S.; Irie, S.; Akita, H. Chem. Pharm. Bull. 1996, 44, 675-680.; Nagumo, S.; Irie, S.; Hayashi, K.; Akita, H. Heterocycles 1996, 43, 1175-1178.
21. (b) Coupling reaction by copper reagent; Nagumo, S.; Irie, S.; Akita, H. J. Chem. Soc., Chem. Commun. 1995, 2001-2002.; Nagumo, S.; Irie, S.; Akita, H. Chem. Pharm. Bull. 1996, 44, 675-680.; Nagumo, S.; Irie, S.; Hayashi, K.; Akita, H. Heterocycles 1996, 43, 1175-1178.
22. (b) Coupling reaction by copper reagent; Nagumo, S.; Irie, S.; Akita, H. J. Chem. Soc., Chem. Commun. 1995, 2001-2002.; Nagumo, S.; Irie, S.; Akita, H. Chem. Pharm. Bull. 1996, 44, 675-680.; Nagumo, S.; Irie, S.; Hayashi, K.; Akita, H. Heterocycles 1996, 43, 1175-1178.
23. Ono, M.; Ogura, Y.; Hatogai, K.; Akita, H. Tetrahedron: Asymmetry 1995, 6, 1829-1832.
24. 7 A detailed procedure will be described elsewhere.
25. Ho, P-T.; Davies, N. Synthesis, 1983, 462.