A short-step synthesis of trans-whisky lactone by an asymmetric Michael reaction

Tetrahedron Asymmetry

Volumn 9, Issue 7, 1998, Pages 1165-1170

  Nishikori, Hisashi ^a   Ito, Katsuji ^b   Katsuki, Tsutomu ^a  

^a KYUSHU UNIVERSITY   (Japan)

^b FUKUOKA UNIVERSITY OF EDUCATION   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

GAMMA LACTONE DERIVATIVE; REAGENT;

ARTICLE; CHEMICAL REACTION; CHIRALITY; CRYSTALLIZATION; ENANTIOMER; PRIORITY JOURNAL; SYNTHESIS;

EID: 0032499189     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00080-9     Document Type: Article

References (40)

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2. (b) Jefford, C. W.; Jaggi, D.; Sledeski, A. W.; Boukouvalas, J. In Studies in Natural Products Chemistry; Atta-er-Rahman, Ed.; Vol. 3, Elsevier: Amsterdam, 1989; pp. 157.
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11. (k) Pelter, A.; Ward, S. R.; Jones, M. D.; Maddocks, P. J. Chem. Soc., Perkin Trans. 1 1993, 2621-2629.
12. For recent Lewis acid catalyzed asymmetric Michael reaction, see: (a) Kobayashi, S.; Suda, S.; Yamada, M.; Mukaiyama, T. Chem. Lett. 1994, 97-100. (b) Shibasaki, M.; Sasai, H.; Arai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 1237-1256.
13. For recent Lewis acid catalyzed asymmetric Michael reaction, see: (a) Kobayashi, S.; Suda, S.; Yamada, M.; Mukaiyama, T. Chem. Lett. 1994, 97-100. (b) Shibasaki, M.; Sasai, H.; Arai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 1237-1256.
14. For examples of the Michael addition reaction of 2-trimethylsiloxyfurans, see: (a) Fukuyama, T.; Yang, L. Tetrahedron Lett. 1986, 27, 6299-6300. (b) Fukuyama, T.; Yang, L. J. Am. Chem. Soc. 1987, 109, 7881-7882. Fukuyama, T.; Yang, L. J. Am. Chem. Soc. 1989, 111, 8303-8304. Brimble, A. M.; Brimble, T. M.; Gibson, J. J. J. Chem. Soc., Perkin Trans. 1. 1989, 179-183. (e) Brimble, A. M.; Duncalf, J. L.; Reid, C. W. D. Tetrahedron: Asymmetry 1995, 6, 263-269. For the examples of other electrophilic substitution reactions, see the following papers and references cited therein: (a) Jefford, W. C.; Jaggi, D.; Bernardinelli, G.; Boukouvalas, J. Tetrahedron Lett. 1987, 28, 4041-4044. (b) Bauer, T. Tetrahedron: Asymmetry 1996, 7, 981-984. Martin, F. S.; Barr, J. K. J. Am. Chem. Soc. 1996, 118, 3299-3300. Castellari, C.; Lombardo, M.; Pietropaolo, G.; Trombini, C. Tetrahedron: Asymmetry 1996, 7, 1059-1068.
15. For examples of the Michael addition reaction of 2-trimethylsiloxyfurans, see: (a) Fukuyama, T.; Yang, L. Tetrahedron Lett. 1986, 27, 6299-6300. (b) Fukuyama, T.; Yang, L. J. Am. Chem. Soc. 1987, 109, 7881-7882. Fukuyama, T.; Yang, L. J. Am. Chem. Soc. 1989, 111, 8303-8304. Brimble, A. M.; Brimble, T. M.; Gibson, J. J. J. Chem. Soc., Perkin Trans. 1. 1989, 179-183. (e) Brimble, A. M.; Duncalf, J. L.; Reid, C. W. D. Tetrahedron: Asymmetry 1995, 6, 263-269. For the examples of other electrophilic substitution reactions, see the following papers and references cited therein: (a) Jefford, W. C.; Jaggi, D.; Bernardinelli, G.; Boukouvalas, J. Tetrahedron Lett. 1987, 28, 4041-4044. (b) Bauer, T. Tetrahedron: Asymmetry 1996, 7, 981-984. Martin, F. S.; Barr, J. K. J. Am. Chem. Soc. 1996, 118, 3299-3300. Castellari, C.; Lombardo, M.; Pietropaolo, G.; Trombini, C. Tetrahedron: Asymmetry 1996, 7, 1059-1068.
16. For examples of the Michael addition reaction of 2-trimethylsiloxyfurans, see: (a) Fukuyama, T.; Yang, L. Tetrahedron Lett. 1986, 27, 6299-6300. (b) Fukuyama, T.; Yang, L. J. Am. Chem. Soc. 1987, 109, 7881-7882. Fukuyama, T.; Yang, L. J. Am. Chem. Soc. 1989, 111, 8303-8304. Brimble, A. M.; Brimble, T. M.; Gibson, J. J. J. Chem. Soc., Perkin Trans. 1. 1989, 179-183. (e) Brimble, A. M.; Duncalf, J. L.; Reid, C. W. D. Tetrahedron: Asymmetry 1995, 6, 263-269. For the examples of other electrophilic substitution reactions, see the following papers and references cited therein: (a) Jefford, W. C.; Jaggi, D.; Bernardinelli, G.; Boukouvalas, J. Tetrahedron Lett. 1987, 28, 4041-4044. (b) Bauer, T. Tetrahedron: Asymmetry 1996, 7, 981-984. Martin, F. S.; Barr, J. K. J. Am. Chem. Soc. 1996, 118, 3299-3300. Castellari, C.; Lombardo, M.; Pietropaolo, G.; Trombini, C. Tetrahedron: Asymmetry 1996, 7, 1059-1068.
17. For examples of the Michael addition reaction of 2-trimethylsiloxyfurans, see: (a) Fukuyama, T.; Yang, L. Tetrahedron Lett. 1986, 27, 6299-6300. (b) Fukuyama, T.; Yang, L. J. Am. Chem. Soc. 1987, 109, 7881-7882. Fukuyama, T.; Yang, L. J. Am. Chem. Soc. 1989, 111, 8303-8304. Brimble, A. M.; Brimble, T. M.; Gibson, J. J. J. Chem. Soc., Perkin Trans. 1. 1989, 179-183. (e) Brimble, A. M.; Duncalf, J. L.; Reid, C. W. D. Tetrahedron: Asymmetry 1995, 6, 263-269. For the examples of other electrophilic substitution reactions, see the following papers and references cited therein: (a) Jefford, W. C.; Jaggi, D.; Bernardinelli, G.; Boukouvalas, J. Tetrahedron Lett. 1987, 28, 4041-4044. (b) Bauer, T. Tetrahedron: Asymmetry 1996, 7, 981-984. Martin, F. S.; Barr, J. K. J. Am. Chem. Soc. 1996, 118, 3299-3300. Castellari, C.; Lombardo, M.; Pietropaolo, G.; Trombini, C. Tetrahedron: Asymmetry 1996, 7, 1059-1068.
18. For examples of the Michael addition reaction of 2-trimethylsiloxyfurans, see: (a) Fukuyama, T.; Yang, L. Tetrahedron Lett. 1986, 27, 6299-6300. (b) Fukuyama, T.; Yang, L. J. Am. Chem. Soc. 1987, 109, 7881-7882. Fukuyama, T.; Yang, L. J. Am. Chem. Soc. 1989, 111, 8303-8304. Brimble, A. M.; Brimble, T. M.; Gibson, J. J. J. Chem. Soc., Perkin Trans. 1. 1989, 179-183. (e) Brimble, A. M.; Duncalf, J. L.; Reid, C. W. D. Tetrahedron: Asymmetry 1995, 6, 263-269. For the examples of other electrophilic substitution reactions, see the following papers and references cited therein: (a) Jefford, W. C.; Jaggi, D.; Bernardinelli, G.; Boukouvalas, J. Tetrahedron Lett. 1987, 28, 4041-4044. (b) Bauer, T. Tetrahedron: Asymmetry 1996, 7, 981-984. Martin, F. S.; Barr, J. K. J. Am. Chem. Soc. 1996, 118, 3299-3300. Castellari, C.; Lombardo, M.; Pietropaolo, G.; Trombini, C. Tetrahedron: Asymmetry 1996, 7, 1059-1068.
19. For examples of the Michael addition reaction of 2-trimethylsiloxyfurans, see: (a) Fukuyama, T.; Yang, L. Tetrahedron Lett. 1986, 27, 6299-6300. (b) Fukuyama, T.; Yang, L. J. Am. Chem. Soc. 1987, 109, 7881-7882. Fukuyama, T.; Yang, L. J. Am. Chem. Soc. 1989, 111, 8303-8304. Brimble, A. M.; Brimble, T. M.; Gibson, J. J. J. Chem. Soc., Perkin Trans. 1. 1989, 179-183. (e) Brimble, A. M.; Duncalf, J. L.; Reid, C. W. D. Tetrahedron: Asymmetry 1995, 6, 263-269. For the examples of other electrophilic substitution reactions, see the following papers and references cited therein: (a) Jefford, W. C.; Jaggi, D.; Bernardinelli, G.; Boukouvalas, J. Tetrahedron Lett. 1987, 28, 4041-4044. (b) Bauer, T. Tetrahedron: Asymmetry 1996, 7, 981-984. Martin, F. S.; Barr, J. K. J. Am. Chem. Soc. 1996, 118, 3299-3300. Castellari, C.; Lombardo, M.; Pietropaolo, G.; Trombini, C. Tetrahedron: Asymmetry 1996, 7, 1059-1068.
20. For examples of the Michael addition reaction of 2-trimethylsiloxyfurans, see: (a) Fukuyama, T.; Yang, L. Tetrahedron Lett. 1986, 27, 6299-6300. (b) Fukuyama, T.; Yang, L. J. Am. Chem. Soc. 1987, 109, 7881-7882. Fukuyama, T.; Yang, L. J. Am. Chem. Soc. 1989, 111, 8303-8304. Brimble, A. M.; Brimble, T. M.; Gibson, J. J. J. Chem. Soc., Perkin Trans. 1. 1989, 179-183. (e) Brimble, A. M.; Duncalf, J. L.; Reid, C. W. D. Tetrahedron: Asymmetry 1995, 6, 263-269. For the examples of other electrophilic substitution reactions, see the following papers and references cited therein: (a) Jefford, W. C.; Jaggi, D.; Bernardinelli, G.; Boukouvalas, J. Tetrahedron Lett. 1987, 28, 4041-4044. (b) Bauer, T. Tetrahedron: Asymmetry 1996, 7, 981-984. Martin, F. S.; Barr, J. K. J. Am. Chem. Soc. 1996, 118, 3299-3300. Castellari, C.; Lombardo, M.; Pietropaolo, G.; Trombini, C. Tetrahedron: Asymmetry 1996, 7, 1059-1068.
21. For examples of the Michael addition reaction of 2-trimethylsiloxyfurans, see: (a) Fukuyama, T.; Yang, L. Tetrahedron Lett. 1986, 27, 6299-6300. (b) Fukuyama, T.; Yang, L. J. Am. Chem. Soc. 1987, 109, 7881-7882. Fukuyama, T.; Yang, L. J. Am. Chem. Soc. 1989, 111, 8303-8304. Brimble, A. M.; Brimble, T. M.; Gibson, J. J. J. Chem. Soc., Perkin Trans. 1. 1989, 179-183. (e) Brimble, A. M.; Duncalf, J. L.; Reid, C. W. D. Tetrahedron: Asymmetry 1995, 6, 263-269. For the examples of other electrophilic substitution reactions, see the following papers and references cited therein: (a) Jefford, W. C.; Jaggi, D.; Bernardinelli, G.; Boukouvalas, J. Tetrahedron Lett. 1987, 28, 4041-4044. (b) Bauer, T. Tetrahedron: Asymmetry 1996, 7, 981-984. Martin, F. S.; Barr, J. K. J. Am. Chem. Soc. 1996, 118, 3299-3300. Castellari, C.; Lombardo, M.; Pietropaolo, G.; Trombini, C. Tetrahedron: Asymmetry 1996, 7, 1059-1068.
22. For examples of the Michael addition reaction of 2-trimethylsiloxyfurans, see: (a) Fukuyama, T.; Yang, L. Tetrahedron Lett. 1986, 27, 6299-6300. (b) Fukuyama, T.; Yang, L. J. Am. Chem. Soc. 1987, 109, 7881-7882. Fukuyama, T.; Yang, L. J. Am. Chem. Soc. 1989, 111, 8303-8304. Brimble, A. M.; Brimble, T. M.; Gibson, J. J. J. Chem. Soc., Perkin Trans. 1. 1989, 179-183. (e) Brimble, A. M.; Duncalf, J. L.; Reid, C. W. D. Tetrahedron: Asymmetry 1995, 6, 263-269. For the examples of other electrophilic substitution reactions, see the following papers and references cited therein: (a) Jefford, W. C.; Jaggi, D.; Bernardinelli, G.; Boukouvalas, J. Tetrahedron Lett. 1987, 28, 4041-4044. (b) Bauer, T. Tetrahedron: Asymmetry 1996, 7, 981-984. Martin, F. S.; Barr, J. K. J. Am. Chem. Soc. 1996, 118, 3299-3300. Castellari, C.; Lombardo, M.; Pietropaolo, G.; Trombini, C. Tetrahedron: Asymmetry 1996, 7, 1059-1068.
23. (a) Kitajima, H.; Katsuki, T. Synlett 1997, 568-570.
24. (b) Kitajima, H.; Ito, K.; Katsuki, T. Tetrahedron 1997, 53, 17015-17028.
25. For isolation of trans- and cis-whisky lactones, see: Otsuka, K.; Zenibayashi, Y.; Itoh, M.; Totsuka, A. Agric. Biol. Chem. 1974, 38, 485-490.
26. For synthesis of optically active trans-whisky lactone, see: (a) Marino, J. P.; de la Pradilla, R. F. Tetrahedron Lett. 1985, 26, 5381-5384. (b) Gunther, C.; Mosandl, A. Liebigs Ann. Chem. 1986, 12, 2112-2122. (c) Beckmann, M.; Hildebrandt, H.; Winterfeldt, E. Tetrahedron: Asymmetry 1990, 1, 335-345. (d) Sharma, G. V.; Vepachdu, S. R.; Chandrasekhar, S. Synth. Commun. 1990, 20, 3403-3410. (e) Casey, M.; Manage, A. C.; Murphy, P. J. Tetrahedron Lett. 1992, 33, 965-968. (f) Miyata, O.; Shinada, T.; Kawakami, N.; Taji, K.; Ninomiya, I.; Naito, T.; Date, T.; Okamura, K. Chem. Pharm. Bull. 1992, 40, 2579-2581. (g) Zschage, O.; Hoppe, D. Tetrahedron 1992, 48, 5657-5666. (h) Ebata, T.; Matsumoto, K.; Yoshikoshi, H.; Koseki, K.; Kawakami, H.; Okano, K.; Matsushita, H. Heterocycles 1993, 36, 1017-1026. (i) Sarmah, B. K.; Barua, N. C. Tetrahedron 1993, 49, 2253-2260. (j) Bloch, R.; Gilbert, L. J. Org. Chem. 1987, 52, 4603-4605. (k) Taber, D. F.; Houze, J. B. J. Org. Chem. 1994, 59, 4004-4006. (1) Pai, Y.-C.; Fang, J.-M.; Wu, S.-H. J. Org. Chem. 1994, 59, 6018-6025. (m) Takahata, H.; Uchida, Y.; Momose, T. J. Org. Chem. 1995, 60, 5628-5633. (n) Ito, K.; Yoshitake, M.; Katsuki, T. Tetrahedron 1996, 52, 3905.
27. For synthesis of optically active trans-whisky lactone, see: (a) Marino, J. P.; de la Pradilla, R. F. Tetrahedron Lett. 1985, 26, 5381-5384. (b) Gunther, C.; Mosandl, A. Liebigs Ann. Chem. 1986, 12, 2112-2122. (c) Beckmann, M.; Hildebrandt, H.; Winterfeldt, E. Tetrahedron: Asymmetry 1990, 1, 335-345. (d) Sharma, G. V.; Vepachdu, S. R.; Chandrasekhar, S. Synth. Commun. 1990, 20, 3403-3410. (e) Casey, M.; Manage, A. C.; Murphy, P. J. Tetrahedron Lett. 1992, 33, 965-968. (f) Miyata, O.; Shinada, T.; Kawakami, N.; Taji, K.; Ninomiya, I.; Naito, T.; Date, T.; Okamura, K. Chem. Pharm. Bull. 1992, 40, 2579-2581. (g) Zschage, O.; Hoppe, D. Tetrahedron 1992, 48, 5657-5666. (h) Ebata, T.; Matsumoto, K.; Yoshikoshi, H.; Koseki, K.; Kawakami, H.; Okano, K.; Matsushita, H. Heterocycles 1993, 36, 1017-1026. (i) Sarmah, B. K.; Barua, N. C. Tetrahedron 1993, 49, 2253-2260. (j) Bloch, R.; Gilbert, L. J. Org. Chem. 1987, 52, 4603-4605. (k) Taber, D. F.; Houze, J. B. J. Org. Chem. 1994, 59, 4004-4006. (1) Pai, Y.-C.; Fang, J.-M.; Wu, S.-H. J. Org. Chem. 1994, 59, 6018-6025. (m) Takahata, H.; Uchida, Y.; Momose, T. J. Org. Chem. 1995, 60, 5628-5633. (n) Ito, K.; Yoshitake, M.; Katsuki, T. Tetrahedron 1996, 52, 3905.
28. For synthesis of optically active trans-whisky lactone, see: (a) Marino, J. P.; de la Pradilla, R. F. Tetrahedron Lett. 1985, 26, 5381-5384. (b) Gunther, C.; Mosandl, A. Liebigs Ann. Chem. 1986, 12, 2112-2122. (c) Beckmann, M.; Hildebrandt, H.; Winterfeldt, E. Tetrahedron: Asymmetry 1990, 1, 335-345. (d) Sharma, G. V.; Vepachdu, S. R.; Chandrasekhar, S. Synth. Commun. 1990, 20, 3403-3410. (e) Casey, M.; Manage, A. C.; Murphy, P. J. Tetrahedron Lett. 1992, 33, 965-968. (f) Miyata, O.; Shinada, T.; Kawakami, N.; Taji, K.; Ninomiya, I.; Naito, T.; Date, T.; Okamura, K. Chem. Pharm. Bull. 1992, 40, 2579-2581. (g) Zschage, O.; Hoppe, D. Tetrahedron 1992, 48, 5657-5666. (h) Ebata, T.; Matsumoto, K.; Yoshikoshi, H.; Koseki, K.; Kawakami, H.; Okano, K.; Matsushita, H. Heterocycles 1993, 36, 1017-1026. (i) Sarmah, B. K.; Barua, N. C. Tetrahedron 1993, 49, 2253-2260. (j) Bloch, R.; Gilbert, L. J. Org. Chem. 1987, 52, 4603-4605. (k) Taber, D. F.; Houze, J. B. J. Org. Chem. 1994, 59, 4004-4006. (1) Pai, Y.-C.; Fang, J.-M.; Wu, S.-H. J. Org. Chem. 1994, 59, 6018-6025. (m) Takahata, H.; Uchida, Y.; Momose, T. J. Org. Chem. 1995, 60, 5628-5633. (n) Ito, K.; Yoshitake, M.; Katsuki, T. Tetrahedron 1996, 52, 3905.
29. For synthesis of optically active trans-whisky lactone, see: (a) Marino, J. P.; de la Pradilla, R. F. Tetrahedron Lett. 1985, 26, 5381-5384. (b) Gunther, C.; Mosandl, A. Liebigs Ann. Chem. 1986, 12, 2112-2122. (c) Beckmann, M.; Hildebrandt, H.; Winterfeldt, E. Tetrahedron: Asymmetry 1990, 1, 335-345. (d) Sharma, G. V.; Vepachdu, S. R.; Chandrasekhar, S. Synth. Commun. 1990, 20, 3403-3410. (e) Casey, M.; Manage, A. C.; Murphy, P. J. Tetrahedron Lett. 1992, 33, 965-968. (f) Miyata, O.; Shinada, T.; Kawakami, N.; Taji, K.; Ninomiya, I.; Naito, T.; Date, T.; Okamura, K. Chem. Pharm. Bull. 1992, 40, 2579-2581. (g) Zschage, O.; Hoppe, D. Tetrahedron 1992, 48, 5657-5666. (h) Ebata, T.; Matsumoto, K.; Yoshikoshi, H.; Koseki, K.; Kawakami, H.; Okano, K.; Matsushita, H. Heterocycles 1993, 36, 1017-1026. (i) Sarmah, B. K.; Barua, N. C. Tetrahedron 1993, 49, 2253-2260. (j) Bloch, R.; Gilbert, L. J. Org. Chem. 1987, 52, 4603-4605. (k) Taber, D. F.; Houze, J. B. J. Org. Chem. 1994, 59, 4004-4006. (1) Pai, Y.-C.; Fang, J.-M.; Wu, S.-H. J. Org. Chem. 1994, 59, 6018-6025. (m) Takahata, H.; Uchida, Y.; Momose, T. J. Org. Chem. 1995, 60, 5628-5633. (n) Ito, K.; Yoshitake, M.; Katsuki, T. Tetrahedron 1996, 52, 3905.
30. For synthesis of optically active trans-whisky lactone, see: (a) Marino, J. P.; de la Pradilla, R. F. Tetrahedron Lett. 1985, 26, 5381-5384. (b) Gunther, C.; Mosandl, A. Liebigs Ann. Chem. 1986, 12, 2112-2122. (c) Beckmann, M.; Hildebrandt, H.; Winterfeldt, E. Tetrahedron: Asymmetry 1990, 1, 335-345. (d) Sharma, G. V.; Vepachdu, S. R.; Chandrasekhar, S. Synth. Commun. 1990, 20, 3403-3410. (e) Casey, M.; Manage, A. C.; Murphy, P. J. Tetrahedron Lett. 1992, 33, 965-968. (f) Miyata, O.; Shinada, T.; Kawakami, N.; Taji, K.; Ninomiya, I.; Naito, T.; Date, T.; Okamura, K. Chem. Pharm. Bull. 1992, 40, 2579-2581. (g) Zschage, O.; Hoppe, D. Tetrahedron 1992, 48, 5657-5666. (h) Ebata, T.; Matsumoto, K.; Yoshikoshi, H.; Koseki, K.; Kawakami, H.; Okano, K.; Matsushita, H. Heterocycles 1993, 36, 1017-1026. (i) Sarmah, B. K.; Barua, N. C. Tetrahedron 1993, 49, 2253-2260. (j) Bloch, R.; Gilbert, L. J. Org. Chem. 1987, 52, 4603-4605. (k) Taber, D. F.; Houze, J. B. J. Org. Chem. 1994, 59, 4004-4006. (1) Pai, Y.-C.; Fang, J.-M.; Wu, S.-H. J. Org. Chem. 1994, 59, 6018-6025. (m) Takahata, H.; Uchida, Y.; Momose, T. J. Org. Chem. 1995, 60, 5628-5633. (n) Ito, K.; Yoshitake, M.; Katsuki, T. Tetrahedron 1996, 52, 3905.
31. For synthesis of optically active trans-whisky lactone, see: (a) Marino, J. P.; de la Pradilla, R. F. Tetrahedron Lett. 1985, 26, 5381-5384. (b) Gunther, C.; Mosandl, A. Liebigs Ann. Chem. 1986, 12, 2112-2122. (c) Beckmann, M.; Hildebrandt, H.; Winterfeldt, E. Tetrahedron: Asymmetry 1990, 1, 335-345. (d) Sharma, G. V.; Vepachdu, S. R.; Chandrasekhar, S. Synth. Commun. 1990, 20, 3403-3410. (e) Casey, M.; Manage, A. C.; Murphy, P. J. Tetrahedron Lett. 1992, 33, 965-968. (f) Miyata, O.; Shinada, T.; Kawakami, N.; Taji, K.; Ninomiya, I.; Naito, T.; Date, T.; Okamura, K. Chem. Pharm. Bull. 1992, 40, 2579-2581. (g) Zschage, O.; Hoppe, D. Tetrahedron 1992, 48, 5657-5666. (h) Ebata, T.; Matsumoto, K.; Yoshikoshi, H.; Koseki, K.; Kawakami, H.; Okano, K.; Matsushita, H. Heterocycles 1993, 36, 1017-1026. (i) Sarmah, B. K.; Barua, N. C. Tetrahedron 1993, 49, 2253-2260. (j) Bloch, R.; Gilbert, L. J. Org. Chem. 1987, 52, 4603-4605. (k) Taber, D. F.; Houze, J. B. J. Org. Chem. 1994, 59, 4004-4006. (1) Pai, Y.-C.; Fang, J.-M.; Wu, S.-H. J. Org. Chem. 1994, 59, 6018-6025. (m) Takahata, H.; Uchida, Y.; Momose, T. J. Org. Chem. 1995, 60, 5628-5633. (n) Ito, K.; Yoshitake, M.; Katsuki, T. Tetrahedron 1996, 52, 3905.
32. For synthesis of optically active trans-whisky lactone, see: (a) Marino, J. P.; de la Pradilla, R. F. Tetrahedron Lett. 1985, 26, 5381-5384. (b) Gunther, C.; Mosandl, A. Liebigs Ann. Chem. 1986, 12, 2112-2122. (c) Beckmann, M.; Hildebrandt, H.; Winterfeldt, E. Tetrahedron: Asymmetry 1990, 1, 335-345. (d) Sharma, G. V.; Vepachdu, S. R.; Chandrasekhar, S. Synth. Commun. 1990, 20, 3403-3410. (e) Casey, M.; Manage, A. C.; Murphy, P. J. Tetrahedron Lett. 1992, 33, 965-968. (f) Miyata, O.; Shinada, T.; Kawakami, N.; Taji, K.; Ninomiya, I.; Naito, T.; Date, T.; Okamura, K. Chem. Pharm. Bull. 1992, 40, 2579-2581. (g) Zschage, O.; Hoppe, D. Tetrahedron 1992, 48, 5657-5666. (h) Ebata, T.; Matsumoto, K.; Yoshikoshi, H.; Koseki, K.; Kawakami, H.; Okano, K.; Matsushita, H. Heterocycles 1993, 36, 1017-1026. (i) Sarmah, B. K.; Barua, N. C. Tetrahedron 1993, 49, 2253-2260. (j) Bloch, R.; Gilbert, L. J. Org. Chem. 1987, 52, 4603-4605. (k) Taber, D. F.; Houze, J. B. J. Org. Chem. 1994, 59, 4004-4006. (1) Pai, Y.-C.; Fang, J.-M.; Wu, S.-H. J. Org. Chem. 1994, 59, 6018-6025. (m) Takahata, H.; Uchida, Y.; Momose, T. J. Org. Chem. 1995, 60, 5628-5633. (n) Ito, K.; Yoshitake, M.; Katsuki, T. Tetrahedron 1996, 52, 3905.
33. For synthesis of optically active trans-whisky lactone, see: (a) Marino, J. P.; de la Pradilla, R. F. Tetrahedron Lett. 1985, 26, 5381-5384. (b) Gunther, C.; Mosandl, A. Liebigs Ann. Chem. 1986, 12, 2112-2122. (c) Beckmann, M.; Hildebrandt, H.; Winterfeldt, E. Tetrahedron: Asymmetry 1990, 1, 335-345. (d) Sharma, G. V.; Vepachdu, S. R.; Chandrasekhar, S. Synth. Commun. 1990, 20, 3403-3410. (e) Casey, M.; Manage, A. C.; Murphy, P. J. Tetrahedron Lett. 1992, 33, 965-968. (f) Miyata, O.; Shinada, T.; Kawakami, N.; Taji, K.; Ninomiya, I.; Naito, T.; Date, T.; Okamura, K. Chem. Pharm. Bull. 1992, 40, 2579-2581. (g) Zschage, O.; Hoppe, D. Tetrahedron 1992, 48, 5657-5666. (h) Ebata, T.; Matsumoto, K.; Yoshikoshi, H.; Koseki, K.; Kawakami, H.; Okano, K.; Matsushita, H. Heterocycles 1993, 36, 1017-1026. (i) Sarmah, B. K.; Barua, N. C. Tetrahedron 1993, 49, 2253-2260. (j) Bloch, R.; Gilbert, L. J. Org. Chem. 1987, 52, 4603-4605. (k) Taber, D. F.; Houze, J. B. J. Org. Chem. 1994, 59, 4004-4006. (1) Pai, Y.-C.; Fang, J.-M.; Wu, S.-H. J. Org. Chem. 1994, 59, 6018-6025. (m) Takahata, H.; Uchida, Y.; Momose, T. J. Org. Chem. 1995, 60, 5628-5633. (n) Ito, K.; Yoshitake, M.; Katsuki, T. Tetrahedron 1996, 52, 3905.
34. For synthesis of optically active trans-whisky lactone, see: (a) Marino, J. P.; de la Pradilla, R. F. Tetrahedron Lett. 1985, 26, 5381-5384. (b) Gunther, C.; Mosandl, A. Liebigs Ann. Chem. 1986, 12, 2112-2122. (c) Beckmann, M.; Hildebrandt, H.; Winterfeldt, E. Tetrahedron: Asymmetry 1990, 1, 335-345. (d) Sharma, G. V.; Vepachdu, S. R.; Chandrasekhar, S. Synth. Commun. 1990, 20, 3403-3410. (e) Casey, M.; Manage, A. C.; Murphy, P. J. Tetrahedron Lett. 1992, 33, 965-968. (f) Miyata, O.; Shinada, T.; Kawakami, N.; Taji, K.; Ninomiya, I.; Naito, T.; Date, T.; Okamura, K. Chem. Pharm. Bull. 1992, 40, 2579-2581. (g) Zschage, O.; Hoppe, D. Tetrahedron 1992, 48, 5657-5666. (h) Ebata, T.; Matsumoto, K.; Yoshikoshi, H.; Koseki, K.; Kawakami, H.; Okano, K.; Matsushita, H. Heterocycles 1993, 36, 1017-1026. (i) Sarmah, B. K.; Barua, N. C. Tetrahedron 1993, 49, 2253-2260. (j) Bloch, R.; Gilbert, L. J. Org. Chem. 1987, 52, 4603-4605. (k) Taber, D. F.; Houze, J. B. J. Org. Chem. 1994, 59, 4004-4006. (1) Pai, Y.-C.; Fang, J.-M.; Wu, S.-H. J. Org. Chem. 1994, 59, 6018-6025. (m) Takahata, H.; Uchida, Y.; Momose, T. J. Org. Chem. 1995, 60, 5628-5633. (n) Ito, K.; Yoshitake, M.; Katsuki, T. Tetrahedron 1996, 52, 3905.
35. For synthesis of optically active trans-whisky lactone, see: (a) Marino, J. P.; de la Pradilla, R. F. Tetrahedron Lett. 1985, 26, 5381-5384. (b) Gunther, C.; Mosandl, A. Liebigs Ann. Chem. 1986, 12, 2112-2122. (c) Beckmann, M.; Hildebrandt, H.; Winterfeldt, E. Tetrahedron: Asymmetry 1990, 1, 335-345. (d) Sharma, G. V.; Vepachdu, S. R.; Chandrasekhar, S. Synth. Commun. 1990, 20, 3403-3410. (e) Casey, M.; Manage, A. C.; Murphy, P. J. Tetrahedron Lett. 1992, 33, 965-968. (f) Miyata, O.; Shinada, T.; Kawakami, N.; Taji, K.; Ninomiya, I.; Naito, T.; Date, T.; Okamura, K. Chem. Pharm. Bull. 1992, 40, 2579-2581. (g) Zschage, O.; Hoppe, D. Tetrahedron 1992, 48, 5657-5666. (h) Ebata, T.; Matsumoto, K.; Yoshikoshi, H.; Koseki, K.; Kawakami, H.; Okano, K.; Matsushita, H. Heterocycles 1993, 36, 1017-1026. (i) Sarmah, B. K.; Barua, N. C. Tetrahedron 1993, 49, 2253-2260. (j) Bloch, R.; Gilbert, L. J. Org. Chem. 1987, 52, 4603-4605. (k) Taber, D. F.; Houze, J. B. J. Org. Chem. 1994, 59, 4004-4006. (1) Pai, Y.-C.; Fang, J.-M.; Wu, S.-H. J. Org. Chem. 1994, 59, 6018-6025. (m) Takahata, H.; Uchida, Y.; Momose, T. J. Org. Chem. 1995, 60, 5628-5633. (n) Ito, K.; Yoshitake, M.; Katsuki, T. Tetrahedron 1996, 52, 3905.
36. For synthesis of optically active trans-whisky lactone, see: (a) Marino, J. P.; de la Pradilla, R. F. Tetrahedron Lett. 1985, 26, 5381-5384. (b) Gunther, C.; Mosandl, A. Liebigs Ann. Chem. 1986, 12, 2112-2122. (c) Beckmann, M.; Hildebrandt, H.; Winterfeldt, E. Tetrahedron: Asymmetry 1990, 1, 335-345. (d) Sharma, G. V.; Vepachdu, S. R.; Chandrasekhar, S. Synth. Commun. 1990, 20, 3403-3410. (e) Casey, M.; Manage, A. C.; Murphy, P. J. Tetrahedron Lett. 1992, 33, 965-968. (f) Miyata, O.; Shinada, T.; Kawakami, N.; Taji, K.; Ninomiya, I.; Naito, T.; Date, T.; Okamura, K. Chem. Pharm. Bull. 1992, 40, 2579-2581. (g) Zschage, O.; Hoppe, D. Tetrahedron 1992, 48, 5657-5666. (h) Ebata, T.; Matsumoto, K.; Yoshikoshi, H.; Koseki, K.; Kawakami, H.; Okano, K.; Matsushita, H. Heterocycles 1993, 36, 1017-1026. (i) Sarmah, B. K.; Barua, N. C. Tetrahedron 1993, 49, 2253-2260. (j) Bloch, R.; Gilbert, L. J. Org. Chem. 1987, 52, 4603-4605. (k) Taber, D. F.; Houze, J. B. J. Org. Chem. 1994, 59, 4004-4006. (1) Pai, Y.-C.; Fang, J.-M.; Wu, S.-H. J. Org. Chem. 1994, 59, 6018-6025. (m) Takahata, H.; Uchida, Y.; Momose, T. J. Org. Chem. 1995, 60, 5628-5633. (n) Ito, K.; Yoshitake, M.; Katsuki, T. Tetrahedron 1996, 52, 3905.
37. For synthesis of optically active trans-whisky lactone, see: (a) Marino, J. P.; de la Pradilla, R. F. Tetrahedron Lett. 1985, 26, 5381-5384. (b) Gunther, C.; Mosandl, A. Liebigs Ann. Chem. 1986, 12, 2112-2122. (c) Beckmann, M.; Hildebrandt, H.; Winterfeldt, E. Tetrahedron: Asymmetry 1990, 1, 335-345. (d) Sharma, G. V.; Vepachdu, S. R.; Chandrasekhar, S. Synth. Commun. 1990, 20, 3403-3410. (e) Casey, M.; Manage, A. C.; Murphy, P. J. Tetrahedron Lett. 1992, 33, 965-968. (f) Miyata, O.; Shinada, T.; Kawakami, N.; Taji, K.; Ninomiya, I.; Naito, T.; Date, T.; Okamura, K. Chem. Pharm. Bull. 1992, 40, 2579-2581. (g) Zschage, O.; Hoppe, D. Tetrahedron 1992, 48, 5657-5666. (h) Ebata, T.; Matsumoto, K.; Yoshikoshi, H.; Koseki, K.; Kawakami, H.; Okano, K.; Matsushita, H. Heterocycles 1993, 36, 1017-1026. (i) Sarmah, B. K.; Barua, N. C. Tetrahedron 1993, 49, 2253-2260. (j) Bloch, R.; Gilbert, L. J. Org. Chem. 1987, 52, 4603-4605. (k) Taber, D. F.; Houze, J. B. J. Org. Chem. 1994, 59, 4004-4006. (1) Pai, Y.-C.; Fang, J.-M.; Wu, S.-H. J. Org. Chem. 1994, 59, 6018-6025. (m) Takahata, H.; Uchida, Y.; Momose, T. J. Org. Chem. 1995, 60, 5628-5633. (n) Ito, K.; Yoshitake, M.; Katsuki, T. Tetrahedron 1996, 52, 3905.
38. For synthesis of optically active trans-whisky lactone, see: (a) Marino, J. P.; de la Pradilla, R. F. Tetrahedron Lett. 1985, 26, 5381-5384. (b) Gunther, C.; Mosandl, A. Liebigs Ann. Chem. 1986, 12, 2112-2122. (c) Beckmann, M.; Hildebrandt, H.; Winterfeldt, E. Tetrahedron: Asymmetry 1990, 1, 335-345. (d) Sharma, G. V.; Vepachdu, S. R.; Chandrasekhar, S. Synth. Commun. 1990, 20, 3403-3410. (e) Casey, M.; Manage, A. C.; Murphy, P. J. Tetrahedron Lett. 1992, 33, 965-968. (f) Miyata, O.; Shinada, T.; Kawakami, N.; Taji, K.; Ninomiya, I.; Naito, T.; Date, T.; Okamura, K. Chem. Pharm. Bull. 1992, 40, 2579-2581. (g) Zschage, O.; Hoppe, D. Tetrahedron 1992, 48, 5657-5666. (h) Ebata, T.; Matsumoto, K.; Yoshikoshi, H.; Koseki, K.; Kawakami, H.; Okano, K.; Matsushita, H. Heterocycles 1993, 36, 1017-1026. (i) Sarmah, B. K.; Barua, N. C. Tetrahedron 1993, 49, 2253-2260. (j) Bloch, R.; Gilbert, L. J. Org. Chem. 1987, 52, 4603-4605. (k) Taber, D. F.; Houze, J. B. J. Org. Chem. 1994, 59, 4004-4006. (1) Pai, Y.-C.; Fang, J.-M.; Wu, S.-H. J. Org. Chem. 1994, 59, 6018-6025. (m) Takahata, H.; Uchida, Y.; Momose, T. J. Org. Chem. 1995, 60, 5628-5633. (n) Ito, K.; Yoshitake, M.; Katsuki, T. Tetrahedron 1996, 52, 3905.
39. For synthesis of optically active trans-whisky lactone, see: (a) Marino, J. P.; de la Pradilla, R. F. Tetrahedron Lett. 1985, 26, 5381-5384. (b) Gunther, C.; Mosandl, A. Liebigs Ann. Chem. 1986, 12, 2112-2122. (c) Beckmann, M.; Hildebrandt, H.; Winterfeldt, E. Tetrahedron: Asymmetry 1990, 1, 335-345. (d) Sharma, G. V.; Vepachdu, S. R.; Chandrasekhar, S. Synth. Commun. 1990, 20, 3403-3410. (e) Casey, M.; Manage, A. C.; Murphy, P. J. Tetrahedron Lett. 1992, 33, 965-968. (f) Miyata, O.; Shinada, T.; Kawakami, N.; Taji, K.; Ninomiya, I.; Naito, T.; Date, T.; Okamura, K. Chem. Pharm. Bull. 1992, 40, 2579-2581. (g) Zschage, O.; Hoppe, D. Tetrahedron 1992, 48, 5657-5666. (h) Ebata, T.; Matsumoto, K.; Yoshikoshi, H.; Koseki, K.; Kawakami, H.; Okano, K.; Matsushita, H. Heterocycles 1993, 36, 1017-1026. (i) Sarmah, B. K.; Barua, N. C. Tetrahedron 1993, 49, 2253-2260. (j) Bloch, R.; Gilbert, L. J. Org. Chem. 1987, 52, 4603-4605. (k) Taber, D. F.; Houze, J. B. J. Org. Chem. 1994, 59, 4004-4006. (1) Pai, Y.-C.; Fang, J.-M.; Wu, S.-H. J. Org. Chem. 1994, 59, 6018-6025. (m) Takahata, H.; Uchida, Y.; Momose, T. J. Org. Chem. 1995, 60, 5628-5633. (n) Ito, K.; Yoshitake, M.; Katsuki, T. Tetrahedron 1996, 52, 3905.
40. Harre, M.; Trabandt, J.; Westermann, J. Liebigs Ann. Chem. 1989, 1081-1083.