Regio- and Stereoselective Functionalization of Linear Dicarboxylic Acid Derivatives. A Sequential Aldol-Lactonization Strategy for the Synthesis of (-)-Roccellaric Acid, (-)-Protolichesterinic Acid, and (-)-Methylenolactocin

Synlett

Volumn 1996, Issue 4, 1996, Pages 343-345

  Sibi, Mukund P ^a   Deshpande, Prasad K ^a   La Loggia, Anthony J ^a  

^a NORTH DAKOTA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002843423     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5427     Document Type: Article

References (46)

1. For selected synthesis of paraconic acids (esters) see: (a) Minami, N.; Kuwajima, I. Tetrahedron Lett. 1977, 1423. (b) Shono, T.; Hamaguchi, H.; Nishiguchi, I.; Sasaki, M. Chem. Lett. 1981, 1217. (c) Pohmakotr, M.; Reutrakul, V.; Phongpradit, T.; Chansri, A. Chem. Lett. 1982, 687. (d) Lawlor, J.; McNamee, M. Tetrahedron Lett. 1983, 24, 2211. (e) Mulzer, J.; Chucholowski, A. Angew. Chem., Int. Ed. Engl. 1986, 25, 655. (f) Alexandre, C.; Rouessac, F. C. R. Acad. Sci. 1982, 785. (g) Banks, M. R.; Dawson, I. M.; Gosney, I.; Hodgson, P. K. G.; Thorburn, P. Tetrahedron Lett. 1995, 36, 3567. (h) de Azevedo, M. B. M.; Murta, M. M.; Greene, A. E. J. Org. Chem. 1992, 57, 4567. (i) Zhu, G.; Lu, X. J. Org. Chem. 1995, 60, 1087. (j) Zhu, G.; Lu, X. Tetrahedron: Asymmetry 1995, 6, 885. (k) Vaupel, A.; Knochel, P. Tetrahedron Lett. 1995, 36, 231. (l) Honda, T.; Kimura, N. J. Chem. Soc., Chem. Commun. 1994, 77. (m) Martin, J.; Watts, P. C.; Johnson, F. J. Org. Chem. 1974, 39, 1676. (n) Murta, M. M.; de Azevedo, M. B. M.; Greene, A. E. J. Org. Chem. 1993, 58, 7537 and references cited therein. (o) Mawson, S. D.; Weavers, R. T. Tetrahedron 1995, 51, 11257.
2. For selected synthesis of paraconic acids (esters) see: (a) Minami, N.; Kuwajima, I. Tetrahedron Lett. 1977, 1423. (b) Shono, T.; Hamaguchi, H.; Nishiguchi, I.; Sasaki, M. Chem. Lett. 1981, 1217. (c) Pohmakotr, M.; Reutrakul, V.; Phongpradit, T.; Chansri, A. Chem. Lett. 1982, 687. (d) Lawlor, J.; McNamee, M. Tetrahedron Lett. 1983, 24, 2211. (e) Mulzer, J.; Chucholowski, A. Angew. Chem., Int. Ed. Engl. 1986, 25, 655. (f) Alexandre, C.; Rouessac, F. C. R. Acad. Sci. 1982, 785. (g) Banks, M. R.; Dawson, I. M.; Gosney, I.; Hodgson, P. K. G.; Thorburn, P. Tetrahedron Lett. 1995, 36, 3567. (h) de Azevedo, M. B. M.; Murta, M. M.; Greene, A. E. J. Org. Chem. 1992, 57, 4567. (i) Zhu, G.; Lu, X. J. Org. Chem. 1995, 60, 1087. (j) Zhu, G.; Lu, X. Tetrahedron: Asymmetry 1995, 6, 885. (k) Vaupel, A.; Knochel, P. Tetrahedron Lett. 1995, 36, 231. (l) Honda, T.; Kimura, N. J. Chem. Soc., Chem. Commun. 1994, 77. (m) Martin, J.; Watts, P. C.; Johnson, F. J. Org. Chem. 1974, 39, 1676. (n) Murta, M. M.; de Azevedo, M. B. M.; Greene, A. E. J. Org. Chem. 1993, 58, 7537 and references cited therein. (o) Mawson, S. D.; Weavers, R. T. Tetrahedron 1995, 51, 11257.
3. For selected synthesis of paraconic acids (esters) see: (a) Minami, N.; Kuwajima, I. Tetrahedron Lett. 1977, 1423. (b) Shono, T.; Hamaguchi, H.; Nishiguchi, I.; Sasaki, M. Chem. Lett. 1981, 1217. (c) Pohmakotr, M.; Reutrakul, V.; Phongpradit, T.; Chansri, A. Chem. Lett. 1982, 687. (d) Lawlor, J.; McNamee, M. Tetrahedron Lett. 1983, 24, 2211. (e) Mulzer, J.; Chucholowski, A. Angew. Chem., Int. Ed. Engl. 1986, 25, 655. (f) Alexandre, C.; Rouessac, F. C. R. Acad. Sci. 1982, 785. (g) Banks, M. R.; Dawson, I. M.; Gosney, I.; Hodgson, P. K. G.; Thorburn, P. Tetrahedron Lett. 1995, 36, 3567. (h) de Azevedo, M. B. M.; Murta, M. M.; Greene, A. E. J. Org. Chem. 1992, 57, 4567. (i) Zhu, G.; Lu, X. J. Org. Chem. 1995, 60, 1087. (j) Zhu, G.; Lu, X. Tetrahedron: Asymmetry 1995, 6, 885. (k) Vaupel, A.; Knochel, P. Tetrahedron Lett. 1995, 36, 231. (l) Honda, T.; Kimura, N. J. Chem. Soc., Chem. Commun. 1994, 77. (m) Martin, J.; Watts, P. C.; Johnson, F. J. Org. Chem. 1974, 39, 1676. (n) Murta, M. M.; de Azevedo, M. B. M.; Greene, A. E. J. Org. Chem. 1993, 58, 7537 and references cited therein. (o) Mawson, S. D.; Weavers, R. T. Tetrahedron 1995, 51, 11257.
4. For selected synthesis of paraconic acids (esters) see: (a) Minami, N.; Kuwajima, I. Tetrahedron Lett. 1977, 1423. (b) Shono, T.; Hamaguchi, H.; Nishiguchi, I.; Sasaki, M. Chem. Lett. 1981, 1217. (c) Pohmakotr, M.; Reutrakul, V.; Phongpradit, T.; Chansri, A. Chem. Lett. 1982, 687. (d) Lawlor, J.; McNamee, M. Tetrahedron Lett. 1983, 24, 2211. (e) Mulzer, J.; Chucholowski, A. Angew. Chem., Int. Ed. Engl. 1986, 25, 655. (f) Alexandre, C.; Rouessac, F. C. R. Acad. Sci. 1982, 785. (g) Banks, M. R.; Dawson, I. M.; Gosney, I.; Hodgson, P. K. G.; Thorburn, P. Tetrahedron Lett. 1995, 36, 3567. (h) de Azevedo, M. B. M.; Murta, M. M.; Greene, A. E. J. Org. Chem. 1992, 57, 4567. (i) Zhu, G.; Lu, X. J. Org. Chem. 1995, 60, 1087. (j) Zhu, G.; Lu, X. Tetrahedron: Asymmetry 1995, 6, 885. (k) Vaupel, A.; Knochel, P. Tetrahedron Lett. 1995, 36, 231. (l) Honda, T.; Kimura, N. J. Chem. Soc., Chem. Commun. 1994, 77. (m) Martin, J.; Watts, P. C.; Johnson, F. J. Org. Chem. 1974, 39, 1676. (n) Murta, M. M.; de Azevedo, M. B. M.; Greene, A. E. J. Org. Chem. 1993, 58, 7537 and references cited therein. (o) Mawson, S. D.; Weavers, R. T. Tetrahedron 1995, 51, 11257.
5. For selected synthesis of paraconic acids (esters) see: (a) Minami, N.; Kuwajima, I. Tetrahedron Lett. 1977, 1423. (b) Shono, T.; Hamaguchi, H.; Nishiguchi, I.; Sasaki, M. Chem. Lett. 1981, 1217. (c) Pohmakotr, M.; Reutrakul, V.; Phongpradit, T.; Chansri, A. Chem. Lett. 1982, 687. (d) Lawlor, J.; McNamee, M. Tetrahedron Lett. 1983, 24, 2211. (e) Mulzer, J.; Chucholowski, A. Angew. Chem., Int. Ed. Engl. 1986, 25, 655. (f) Alexandre, C.; Rouessac, F. C. R. Acad. Sci. 1982, 785. (g) Banks, M. R.; Dawson, I. M.; Gosney, I.; Hodgson, P. K. G.; Thorburn, P. Tetrahedron Lett. 1995, 36, 3567. (h) de Azevedo, M. B. M.; Murta, M. M.; Greene, A. E. J. Org. Chem. 1992, 57, 4567. (i) Zhu, G.; Lu, X. J. Org. Chem. 1995, 60, 1087. (j) Zhu, G.; Lu, X. Tetrahedron: Asymmetry 1995, 6, 885. (k) Vaupel, A.; Knochel, P. Tetrahedron Lett. 1995, 36, 231. (l) Honda, T.; Kimura, N. J. Chem. Soc., Chem. Commun. 1994, 77. (m) Martin, J.; Watts, P. C.; Johnson, F. J. Org. Chem. 1974, 39, 1676. (n) Murta, M. M.; de Azevedo, M. B. M.; Greene, A. E. J. Org. Chem. 1993, 58, 7537 and references cited therein. (o) Mawson, S. D.; Weavers, R. T. Tetrahedron 1995, 51, 11257.
6. For selected synthesis of paraconic acids (esters) see: (a) Minami, N.; Kuwajima, I. Tetrahedron Lett. 1977, 1423. (b) Shono, T.; Hamaguchi, H.; Nishiguchi, I.; Sasaki, M. Chem. Lett. 1981, 1217. (c) Pohmakotr, M.; Reutrakul, V.; Phongpradit, T.; Chansri, A. Chem. Lett. 1982, 687. (d) Lawlor, J.; McNamee, M. Tetrahedron Lett. 1983, 24, 2211. (e) Mulzer, J.; Chucholowski, A. Angew. Chem., Int. Ed. Engl. 1986, 25, 655. (f) Alexandre, C.; Rouessac, F. C. R. Acad. Sci. 1982, 785. (g) Banks, M. R.; Dawson, I. M.; Gosney, I.; Hodgson, P. K. G.; Thorburn, P. Tetrahedron Lett. 1995, 36, 3567. (h) de Azevedo, M. B. M.; Murta, M. M.; Greene, A. E. J. Org. Chem. 1992, 57, 4567. (i) Zhu, G.; Lu, X. J. Org. Chem. 1995, 60, 1087. (j) Zhu, G.; Lu, X. Tetrahedron: Asymmetry 1995, 6, 885. (k) Vaupel, A.; Knochel, P. Tetrahedron Lett. 1995, 36, 231. (l) Honda, T.; Kimura, N. J. Chem. Soc., Chem. Commun. 1994, 77. (m) Martin, J.; Watts, P. C.; Johnson, F. J. Org. Chem. 1974, 39, 1676. (n) Murta, M. M.; de Azevedo, M. B. M.; Greene, A. E. J. Org. Chem. 1993, 58, 7537 and references cited therein. (o) Mawson, S. D.; Weavers, R. T. Tetrahedron 1995, 51, 11257.
7. For selected synthesis of paraconic acids (esters) see: (a) Minami, N.; Kuwajima, I. Tetrahedron Lett. 1977, 1423. (b) Shono, T.; Hamaguchi, H.; Nishiguchi, I.; Sasaki, M. Chem. Lett. 1981, 1217. (c) Pohmakotr, M.; Reutrakul, V.; Phongpradit, T.; Chansri, A. Chem. Lett. 1982, 687. (d) Lawlor, J.; McNamee, M. Tetrahedron Lett. 1983, 24, 2211. (e) Mulzer, J.; Chucholowski, A. Angew. Chem., Int. Ed. Engl. 1986, 25, 655. (f) Alexandre, C.; Rouessac, F. C. R. Acad. Sci. 1982, 785. (g) Banks, M. R.; Dawson, I. M.; Gosney, I.; Hodgson, P. K. G.; Thorburn, P. Tetrahedron Lett. 1995, 36, 3567. (h) de Azevedo, M. B. M.; Murta, M. M.; Greene, A. E. J. Org. Chem. 1992, 57, 4567. (i) Zhu, G.; Lu, X. J. Org. Chem. 1995, 60, 1087. (j) Zhu, G.; Lu, X. Tetrahedron: Asymmetry 1995, 6, 885. (k) Vaupel, A.; Knochel, P. Tetrahedron Lett. 1995, 36, 231. (l) Honda, T.; Kimura, N. J. Chem. Soc., Chem. Commun. 1994, 77. (m) Martin, J.; Watts, P. C.; Johnson, F. J. Org. Chem. 1974, 39, 1676. (n) Murta, M. M.; de Azevedo, M. B. M.; Greene, A. E. J. Org. Chem. 1993, 58, 7537 and references cited therein. (o) Mawson, S. D.; Weavers, R. T. Tetrahedron 1995, 51, 11257.
8. For selected synthesis of paraconic acids (esters) see: (a) Minami, N.; Kuwajima, I. Tetrahedron Lett. 1977, 1423. (b) Shono, T.; Hamaguchi, H.; Nishiguchi, I.; Sasaki, M. Chem. Lett. 1981, 1217. (c) Pohmakotr, M.; Reutrakul, V.; Phongpradit, T.; Chansri, A. Chem. Lett. 1982, 687. (d) Lawlor, J.; McNamee, M. Tetrahedron Lett. 1983, 24, 2211. (e) Mulzer, J.; Chucholowski, A. Angew. Chem., Int. Ed. Engl. 1986, 25, 655. (f) Alexandre, C.; Rouessac, F. C. R. Acad. Sci. 1982, 785. (g) Banks, M. R.; Dawson, I. M.; Gosney, I.; Hodgson, P. K. G.; Thorburn, P. Tetrahedron Lett. 1995, 36, 3567. (h) de Azevedo, M. B. M.; Murta, M. M.; Greene, A. E. J. Org. Chem. 1992, 57, 4567. (i) Zhu, G.; Lu, X. J. Org. Chem. 1995, 60, 1087. (j) Zhu, G.; Lu, X. Tetrahedron: Asymmetry 1995, 6, 885. (k) Vaupel, A.; Knochel, P. Tetrahedron Lett. 1995, 36, 231. (l) Honda, T.; Kimura, N. J. Chem. Soc., Chem. Commun. 1994, 77. (m) Martin, J.; Watts, P. C.; Johnson, F. J. Org. Chem. 1974, 39, 1676. (n) Murta, M. M.; de Azevedo, M. B. M.; Greene, A. E. J. Org. Chem. 1993, 58, 7537 and references cited therein. (o) Mawson, S. D.; Weavers, R. T. Tetrahedron 1995, 51, 11257.
9. For selected synthesis of paraconic acids (esters) see: (a) Minami, N.; Kuwajima, I. Tetrahedron Lett. 1977, 1423. (b) Shono, T.; Hamaguchi, H.; Nishiguchi, I.; Sasaki, M. Chem. Lett. 1981, 1217. (c) Pohmakotr, M.; Reutrakul, V.; Phongpradit, T.; Chansri, A. Chem. Lett. 1982, 687. (d) Lawlor, J.; McNamee, M. Tetrahedron Lett. 1983, 24, 2211. (e) Mulzer, J.; Chucholowski, A. Angew. Chem., Int. Ed. Engl. 1986, 25, 655. (f) Alexandre, C.; Rouessac, F. C. R. Acad. Sci. 1982, 785. (g) Banks, M. R.; Dawson, I. M.; Gosney, I.; Hodgson, P. K. G.; Thorburn, P. Tetrahedron Lett. 1995, 36, 3567. (h) de Azevedo, M. B. M.; Murta, M. M.; Greene, A. E. J. Org. Chem. 1992, 57, 4567. (i) Zhu, G.; Lu, X. J. Org. Chem. 1995, 60, 1087. (j) Zhu, G.; Lu, X. Tetrahedron: Asymmetry 1995, 6, 885. (k) Vaupel, A.; Knochel, P. Tetrahedron Lett. 1995, 36, 231. (l) Honda, T.; Kimura, N. J. Chem. Soc., Chem. Commun. 1994, 77. (m) Martin, J.; Watts, P. C.; Johnson, F. J. Org. Chem. 1974, 39, 1676. (n) Murta, M. M.; de Azevedo, M. B. M.; Greene, A. E. J. Org. Chem. 1993, 58, 7537 and references cited therein. (o) Mawson, S. D.; Weavers, R. T. Tetrahedron 1995, 51, 11257.
10. For selected synthesis of paraconic acids (esters) see: (a) Minami, N.; Kuwajima, I. Tetrahedron Lett. 1977, 1423. (b) Shono, T.; Hamaguchi, H.; Nishiguchi, I.; Sasaki, M. Chem. Lett. 1981, 1217. (c) Pohmakotr, M.; Reutrakul, V.; Phongpradit, T.; Chansri, A. Chem. Lett. 1982, 687. (d) Lawlor, J.; McNamee, M. Tetrahedron Lett. 1983, 24, 2211. (e) Mulzer, J.; Chucholowski, A. Angew. Chem., Int. Ed. Engl. 1986, 25, 655. (f) Alexandre, C.; Rouessac, F. C. R. Acad. Sci. 1982, 785. (g) Banks, M. R.; Dawson, I. M.; Gosney, I.; Hodgson, P. K. G.; Thorburn, P. Tetrahedron Lett. 1995, 36, 3567. (h) de Azevedo, M. B. M.; Murta, M. M.; Greene, A. E. J. Org. Chem. 1992, 57, 4567. (i) Zhu, G.; Lu, X. J. Org. Chem. 1995, 60, 1087. (j) Zhu, G.; Lu, X. Tetrahedron: Asymmetry 1995, 6, 885. (k) Vaupel, A.; Knochel, P. Tetrahedron Lett. 1995, 36, 231. (l) Honda, T.; Kimura, N. J. Chem. Soc., Chem. Commun. 1994, 77. (m) Martin, J.; Watts, P. C.; Johnson, F. J. Org. Chem. 1974, 39, 1676. (n) Murta, M. M.; de Azevedo, M. B. M.; Greene, A. E. J. Org. Chem. 1993, 58, 7537 and references cited therein. (o) Mawson, S. D.; Weavers, R. T. Tetrahedron 1995, 51, 11257.
11. For selected synthesis of paraconic acids (esters) see: (a) Minami, N.; Kuwajima, I. Tetrahedron Lett. 1977, 1423. (b) Shono, T.; Hamaguchi, H.; Nishiguchi, I.; Sasaki, M. Chem. Lett. 1981, 1217. (c) Pohmakotr, M.; Reutrakul, V.; Phongpradit, T.; Chansri, A. Chem. Lett. 1982, 687. (d) Lawlor, J.; McNamee, M. Tetrahedron Lett. 1983, 24, 2211. (e) Mulzer, J.; Chucholowski, A. Angew. Chem., Int. Ed. Engl. 1986, 25, 655. (f) Alexandre, C.; Rouessac, F. C. R. Acad. Sci. 1982, 785. (g) Banks, M. R.; Dawson, I. M.; Gosney, I.; Hodgson, P. K. G.; Thorburn, P. Tetrahedron Lett. 1995, 36, 3567. (h) de Azevedo, M. B. M.; Murta, M. M.; Greene, A. E. J. Org. Chem. 1992, 57, 4567. (i) Zhu, G.; Lu, X. J. Org. Chem. 1995, 60, 1087. (j) Zhu, G.; Lu, X. Tetrahedron: Asymmetry 1995, 6, 885. (k) Vaupel, A.; Knochel, P. Tetrahedron Lett. 1995, 36, 231. (l) Honda, T.; Kimura, N. J. Chem. Soc., Chem. Commun. 1994, 77. (m) Martin, J.; Watts, P. C.; Johnson, F. J. Org. Chem. 1974, 39, 1676. (n) Murta, M. M.; de Azevedo, M. B. M.; Greene, A. E. J. Org. Chem. 1993, 58, 7537 and references cited therein. (o) Mawson, S. D.; Weavers, R. T. Tetrahedron 1995, 51, 11257.
12. For selected synthesis of paraconic acids (esters) see: (a) Minami, N.; Kuwajima, I. Tetrahedron Lett. 1977, 1423. (b) Shono, T.; Hamaguchi, H.; Nishiguchi, I.; Sasaki, M. Chem. Lett. 1981, 1217. (c) Pohmakotr, M.; Reutrakul, V.; Phongpradit, T.; Chansri, A. Chem. Lett. 1982, 687. (d) Lawlor, J.; McNamee, M. Tetrahedron Lett. 1983, 24, 2211. (e) Mulzer, J.; Chucholowski, A. Angew. Chem., Int. Ed. Engl. 1986, 25, 655. (f) Alexandre, C.; Rouessac, F. C. R. Acad. Sci. 1982, 785. (g) Banks, M. R.; Dawson, I. M.; Gosney, I.; Hodgson, P. K. G.; Thorburn, P. Tetrahedron Lett. 1995, 36, 3567. (h) de Azevedo, M. B. M.; Murta, M. M.; Greene, A. E. J. Org. Chem. 1992, 57, 4567. (i) Zhu, G.; Lu, X. J. Org. Chem. 1995, 60, 1087. (j) Zhu, G.; Lu, X. Tetrahedron: Asymmetry 1995, 6, 885. (k) Vaupel, A.; Knochel, P. Tetrahedron Lett. 1995, 36, 231. (l) Honda, T.; Kimura, N. J. Chem. Soc., Chem. Commun. 1994, 77. (m) Martin, J.; Watts, P. C.; Johnson, F. J. Org. Chem. 1974, 39, 1676. (n) Murta, M. M.; de Azevedo, M. B. M.; Greene, A. E. J. Org. Chem. 1993, 58, 7537 and references cited therein. (o) Mawson, S. D.; Weavers, R. T. Tetrahedron 1995, 51, 11257.
13. For selected synthesis of paraconic acids (esters) see: (a) Minami, N.; Kuwajima, I. Tetrahedron Lett. 1977, 1423. (b) Shono, T.; Hamaguchi, H.; Nishiguchi, I.; Sasaki, M. Chem. Lett. 1981, 1217. (c) Pohmakotr, M.; Reutrakul, V.; Phongpradit, T.; Chansri, A. Chem. Lett. 1982, 687. (d) Lawlor, J.; McNamee, M. Tetrahedron Lett. 1983, 24, 2211. (e) Mulzer, J.; Chucholowski, A. Angew. Chem., Int. Ed. Engl. 1986, 25, 655. (f) Alexandre, C.; Rouessac, F. C. R. Acad. Sci. 1982, 785. (g) Banks, M. R.; Dawson, I. M.; Gosney, I.; Hodgson, P. K. G.; Thorburn, P. Tetrahedron Lett. 1995, 36, 3567. (h) de Azevedo, M. B. M.; Murta, M. M.; Greene, A. E. J. Org. Chem. 1992, 57, 4567. (i) Zhu, G.; Lu, X. J. Org. Chem. 1995, 60, 1087. (j) Zhu, G.; Lu, X. Tetrahedron: Asymmetry 1995, 6, 885. (k) Vaupel, A.; Knochel, P. Tetrahedron Lett. 1995, 36, 231. (l) Honda, T.; Kimura, N. J. Chem. Soc., Chem. Commun. 1994, 77. (m) Martin, J.; Watts, P. C.; Johnson, F. J. Org. Chem. 1974, 39, 1676. (n) Murta, M. M.; de Azevedo, M. B. M.; Greene, A. E. J. Org. Chem. 1993, 58, 7537 and references cited therein. (o) Mawson, S. D.; Weavers, R. T. Tetrahedron 1995, 51, 11257.
14. For selected synthesis of paraconic acids (esters) see: (a) Minami, N.; Kuwajima, I. Tetrahedron Lett. 1977, 1423. (b) Shono, T.; Hamaguchi, H.; Nishiguchi, I.; Sasaki, M. Chem. Lett. 1981, 1217. (c) Pohmakotr, M.; Reutrakul, V.; Phongpradit, T.; Chansri, A. Chem. Lett. 1982, 687. (d) Lawlor, J.; McNamee, M. Tetrahedron Lett. 1983, 24, 2211. (e) Mulzer, J.; Chucholowski, A. Angew. Chem., Int. Ed. Engl. 1986, 25, 655. (f) Alexandre, C.; Rouessac, F. C. R. Acad. Sci. 1982, 785. (g) Banks, M. R.; Dawson, I. M.; Gosney, I.; Hodgson, P. K. G.; Thorburn, P. Tetrahedron Lett. 1995, 36, 3567. (h) de Azevedo, M. B. M.; Murta, M. M.; Greene, A. E. J. Org. Chem. 1992, 57, 4567. (i) Zhu, G.; Lu, X. J. Org. Chem. 1995, 60, 1087. (j) Zhu, G.; Lu, X. Tetrahedron: Asymmetry 1995, 6, 885. (k) Vaupel, A.; Knochel, P. Tetrahedron Lett. 1995, 36, 231. (l) Honda, T.; Kimura, N. J. Chem. Soc., Chem. Commun. 1994, 77. (m) Martin, J.; Watts, P. C.; Johnson, F. J. Org. Chem. 1974, 39, 1676. (n) Murta, M. M.; de Azevedo, M. B. M.; Greene, A. E. J. Org. Chem. 1993, 58, 7537 and references cited therein. (o) Mawson, S. D.; Weavers, R. T. Tetrahedron 1995, 51, 11257.
15. For selected synthesis of paraconic acids (esters) see: (a) Minami, N.; Kuwajima, I. Tetrahedron Lett. 1977, 1423. (b) Shono, T.; Hamaguchi, H.; Nishiguchi, I.; Sasaki, M. Chem. Lett. 1981, 1217. (c) Pohmakotr, M.; Reutrakul, V.; Phongpradit, T.; Chansri, A. Chem. Lett. 1982, 687. (d) Lawlor, J.; McNamee, M. Tetrahedron Lett. 1983, 24, 2211. (e) Mulzer, J.; Chucholowski, A. Angew. Chem., Int. Ed. Engl. 1986, 25, 655. (f) Alexandre, C.; Rouessac, F. C. R. Acad. Sci. 1982, 785. (g) Banks, M. R.; Dawson, I. M.; Gosney, I.; Hodgson, P. K. G.; Thorburn, P. Tetrahedron Lett. 1995, 36, 3567. (h) de Azevedo, M. B. M.; Murta, M. M.; Greene, A. E. J. Org. Chem. 1992, 57, 4567. (i) Zhu, G.; Lu, X. J. Org. Chem. 1995, 60, 1087. (j) Zhu, G.; Lu, X. Tetrahedron: Asymmetry 1995, 6, 885. (k) Vaupel, A.; Knochel, P. Tetrahedron Lett. 1995, 36, 231. (l) Honda, T.; Kimura, N. J. Chem. Soc., Chem. Commun. 1994, 77. (m) Martin, J.; Watts, P. C.; Johnson, F. J. Org. Chem. 1974, 39, 1676. (n) Murta, M. M.; de Azevedo, M. B. M.; Greene, A. E. J. Org. Chem. 1993, 58, 7537 and references cited therein. (o) Mawson, S. D.; Weavers, R. T. Tetrahedron 1995, 51, 11257.
16. Park, B. K.; Nakagawa, M.; Hirota, A.; Nakayama, M. J. Antibiot. 1988, 41, 751
17. Reference 1n and references cited therein.
18. (a) Magnuson, S. R. Tetrahedron 1995, 51, 2167 and references therein.
19. (b) Poss, C. A.; Schreiber, S. L. Acc. Chem. Res. 1994, 27, 9.
20. For selected examples on the synthesis of butyrolactones with biological activity see: (a) Brown, H. C.; Kulkarni, S. V.; Racherla, U S. J. Org. Chem. 1994, 59, 365 and references therein. (b) Shimada, S.; Hashimoto, Y.; Saigo, K. J. Org. Chem. 1993, 58, 5226. (c) Nagau, Y.; Dai, W-M.; Ochiai, M.; Shiro, M. J. Org. Chem. 1989, 54, 5211. (d) Nakamura, E.; Oshino, H.; Kuwajima, I. J. Am. Chem. Soc. 1986, 108, 3745. (e) Hannesian, S.; Cooke, N. G.; DeHoff, B.; Sakito, Y. J. Am. Chem. Soc. 1990, 112, 5276. (f) Mandal, A. K.; Mahajan, S. W. Synthesis 1991, 311. (g) Chan, P. C.-M.; Chong, J. M. Tetrahedron Lett. 1990, 31, 1981. (h) Ohkuma, T.; Kitamura, M.; Noyori, R. Tetrahedron Lett. 1990, 31, 5509. (i) Sibi, M. P.; Gaboury, J. A. Tetrahedron Lett. 1992, 33, 5681.
21. For selected examples on the synthesis of butyrolactones with biological activity see: (a) Brown, H. C.; Kulkarni, S. V.; Racherla, U S. J. Org. Chem. 1994, 59, 365 and references therein. (b) Shimada, S.; Hashimoto, Y.; Saigo, K. J. Org. Chem. 1993, 58, 5226. (c) Nagau, Y.; Dai, W-M.; Ochiai, M.; Shiro, M. J. Org. Chem. 1989, 54, 5211. (d) Nakamura, E.; Oshino, H.; Kuwajima, I. J. Am. Chem. Soc. 1986, 108, 3745. (e) Hannesian, S.; Cooke, N. G.; DeHoff, B.; Sakito, Y. J. Am. Chem. Soc. 1990, 112, 5276. (f) Mandal, A. K.; Mahajan, S. W. Synthesis 1991, 311. (g) Chan, P. C.-M.; Chong, J. M. Tetrahedron Lett. 1990, 31, 1981. (h) Ohkuma, T.; Kitamura, M.; Noyori, R. Tetrahedron Lett. 1990, 31, 5509. (i) Sibi, M. P.; Gaboury, J. A. Tetrahedron Lett. 1992, 33, 5681.
22. For selected examples on the synthesis of butyrolactones with biological activity see: (a) Brown, H. C.; Kulkarni, S. V.; Racherla, U S. J. Org. Chem. 1994, 59, 365 and references therein. (b) Shimada, S.; Hashimoto, Y.; Saigo, K. J. Org. Chem. 1993, 58, 5226. (c) Nagau, Y.; Dai, W-M.; Ochiai, M.; Shiro, M. J. Org. Chem. 1989, 54, 5211. (d) Nakamura, E.; Oshino, H.; Kuwajima, I. J. Am. Chem. Soc. 1986, 108, 3745. (e) Hannesian, S.; Cooke, N. G.; DeHoff, B.; Sakito, Y. J. Am. Chem. Soc. 1990, 112, 5276. (f) Mandal, A. K.; Mahajan, S. W. Synthesis 1991, 311. (g) Chan, P. C.-M.; Chong, J. M. Tetrahedron Lett. 1990, 31, 1981. (h) Ohkuma, T.; Kitamura, M.; Noyori, R. Tetrahedron Lett. 1990, 31, 5509. (i) Sibi, M. P.; Gaboury, J. A. Tetrahedron Lett. 1992, 33, 5681.
23. For selected examples on the synthesis of butyrolactones with biological activity see: (a) Brown, H. C.; Kulkarni, S. V.; Racherla, U S. J. Org. Chem. 1994, 59, 365 and references therein. (b) Shimada, S.; Hashimoto, Y.; Saigo, K. J. Org. Chem. 1993, 58, 5226. (c) Nagau, Y.; Dai, W-M.; Ochiai, M.; Shiro, M. J. Org. Chem. 1989, 54, 5211. (d) Nakamura, E.; Oshino, H.; Kuwajima, I. J. Am. Chem. Soc. 1986, 108, 3745. (e) Hannesian, S.; Cooke, N. G.; DeHoff, B.; Sakito, Y. J. Am. Chem. Soc. 1990, 112, 5276. (f) Mandal, A. K.; Mahajan, S. W. Synthesis 1991, 311. (g) Chan, P. C.-M.; Chong, J. M. Tetrahedron Lett. 1990, 31, 1981. (h) Ohkuma, T.; Kitamura, M.; Noyori, R. Tetrahedron Lett. 1990, 31, 5509. (i) Sibi, M. P.; Gaboury, J. A. Tetrahedron Lett. 1992, 33, 5681.
24. For selected examples on the synthesis of butyrolactones with biological activity see: (a) Brown, H. C.; Kulkarni, S. V.; Racherla, U S. J. Org. Chem. 1994, 59, 365 and references therein. (b) Shimada, S.; Hashimoto, Y.; Saigo, K. J. Org. Chem. 1993, 58, 5226. (c) Nagau, Y.; Dai, W-M.; Ochiai, M.; Shiro, M. J. Org. Chem. 1989, 54, 5211. (d) Nakamura, E.; Oshino, H.; Kuwajima, I. J. Am. Chem. Soc. 1986, 108, 3745. (e) Hannesian, S.; Cooke, N. G.; DeHoff, B.; Sakito, Y. J. Am. Chem. Soc. 1990, 112, 5276. (f) Mandal, A. K.; Mahajan, S. W. Synthesis 1991, 311. (g) Chan, P. C.-M.; Chong, J. M. Tetrahedron Lett. 1990, 31, 1981. (h) Ohkuma, T.; Kitamura, M.; Noyori, R. Tetrahedron Lett. 1990, 31, 5509. (i) Sibi, M. P.; Gaboury, J. A. Tetrahedron Lett. 1992, 33, 5681.
25. For selected examples on the synthesis of butyrolactones with biological activity see: (a) Brown, H. C.; Kulkarni, S. V.; Racherla, U S. J. Org. Chem. 1994, 59, 365 and references therein. (b) Shimada, S.; Hashimoto, Y.; Saigo, K. J. Org. Chem. 1993, 58, 5226. (c) Nagau, Y.; Dai, W-M.; Ochiai, M.; Shiro, M. J. Org. Chem. 1989, 54, 5211. (d) Nakamura, E.; Oshino, H.; Kuwajima, I. J. Am. Chem. Soc. 1986, 108, 3745. (e) Hannesian, S.; Cooke, N. G.; DeHoff, B.; Sakito, Y. J. Am. Chem. Soc. 1990, 112, 5276. (f) Mandal, A. K.; Mahajan, S. W. Synthesis 1991, 311. (g) Chan, P. C.-M.; Chong, J. M. Tetrahedron Lett. 1990, 31, 1981. (h) Ohkuma, T.; Kitamura, M.; Noyori, R. Tetrahedron Lett. 1990, 31, 5509. (i) Sibi, M. P.; Gaboury, J. A. Tetrahedron Lett. 1992, 33, 5681.
26. For selected examples on the synthesis of butyrolactones with biological activity see: (a) Brown, H. C.; Kulkarni, S. V.; Racherla, U S. J. Org. Chem. 1994, 59, 365 and references therein. (b) Shimada, S.; Hashimoto, Y.; Saigo, K. J. Org. Chem. 1993, 58, 5226. (c) Nagau, Y.; Dai, W-M.; Ochiai, M.; Shiro, M. J. Org. Chem. 1989, 54, 5211. (d) Nakamura, E.; Oshino, H.; Kuwajima, I. J. Am. Chem. Soc. 1986, 108, 3745. (e) Hannesian, S.; Cooke, N. G.; DeHoff, B.; Sakito, Y. J. Am. Chem. Soc. 1990, 112, 5276. (f) Mandal, A. K.; Mahajan, S. W. Synthesis 1991, 311. (g) Chan, P. C.-M.; Chong, J. M. Tetrahedron Lett. 1990, 31, 1981. (h) Ohkuma, T.; Kitamura, M.; Noyori, R. Tetrahedron Lett. 1990, 31, 5509. (i) Sibi, M. P.; Gaboury, J. A. Tetrahedron Lett. 1992, 33, 5681.
27. For selected examples on the synthesis of butyrolactones with biological activity see: (a) Brown, H. C.; Kulkarni, S. V.; Racherla, U S. J. Org. Chem. 1994, 59, 365 and references therein. (b) Shimada, S.; Hashimoto, Y.; Saigo, K. J. Org. Chem. 1993, 58, 5226. (c) Nagau, Y.; Dai, W-M.; Ochiai, M.; Shiro, M. J. Org. Chem. 1989, 54, 5211. (d) Nakamura, E.; Oshino, H.; Kuwajima, I. J. Am. Chem. Soc. 1986, 108, 3745. (e) Hannesian, S.; Cooke, N. G.; DeHoff, B.; Sakito, Y. J. Am. Chem. Soc. 1990, 112, 5276. (f) Mandal, A. K.; Mahajan, S. W. Synthesis 1991, 311. (g) Chan, P. C.-M.; Chong, J. M. Tetrahedron Lett. 1990, 31, 1981. (h) Ohkuma, T.; Kitamura, M.; Noyori, R. Tetrahedron Lett. 1990, 31, 5509. (i) Sibi, M. P.; Gaboury, J. A. Tetrahedron Lett. 1992, 33, 5681.
28. For selected examples on the synthesis of butyrolactones with biological activity see: (a) Brown, H. C.; Kulkarni, S. V.; Racherla, U S. J. Org. Chem. 1994, 59, 365 and references therein. (b) Shimada, S.; Hashimoto, Y.; Saigo, K. J. Org. Chem. 1993, 58, 5226. (c) Nagau, Y.; Dai, W-M.; Ochiai, M.; Shiro, M. J. Org. Chem. 1989, 54, 5211. (d) Nakamura, E.; Oshino, H.; Kuwajima, I. J. Am. Chem. Soc. 1986, 108, 3745. (e) Hannesian, S.; Cooke, N. G.; DeHoff, B.; Sakito, Y. J. Am. Chem. Soc. 1990, 112, 5276. (f) Mandal, A. K.; Mahajan, S. W. Synthesis 1991, 311. (g) Chan, P. C.-M.; Chong, J. M. Tetrahedron Lett. 1990, 31, 1981. (h) Ohkuma, T.; Kitamura, M.; Noyori, R. Tetrahedron Lett. 1990, 31, 5509. (i) Sibi, M. P.; Gaboury, J. A. Tetrahedron Lett. 1992, 33, 5681.
29. (a) Sibi, M. P.; Deshpande, P. K.; La Loggia, A. J.; Christensen, J. W. Tetrahedron Lett. in press.
30. For the use of this auxiliary in aldol, alkylation, Diels-Alder, and radical reactions see: (b) Sibi, M. P.; Deshpande, P. K.; Ji, J. Tetrahedron Lett. in press. (c) Sibi, M. P.; Jasperse, C. P.; Ji, J. J. Am. Chem. Soc. 1995, 117, 10779. (d) Sibi, M. P.; Ji, J. Angew. Chem., Int. Ed. Engl. 1996, 36, 0000.
31. For the use of this auxiliary in aldol, alkylation, Diels-Alder, and radical reactions see: (b) Sibi, M. P.; Deshpande, P. K.; Ji, J. Tetrahedron Lett. in press. (c) Sibi, M. P.; Jasperse, C. P.; Ji, J. J. Am. Chem. Soc. 1995, 117, 10779. (d) Sibi, M. P.; Ji, J. Angew. Chem., Int. Ed. Engl. 1996, 36, 0000.
32. For the use of this auxiliary in aldol, alkylation, Diels-Alder, and radical reactions see: (b) Sibi, M. P.; Deshpande, P. K.; Ji, J. Tetrahedron Lett. in press. (c) Sibi, M. P.; Jasperse, C. P.; Ji, J. J. Am. Chem. Soc. 1995, 117, 10779. (d) Sibi, M. P.; Ji, J. Angew. Chem., Int. Ed. Engl. 1996, 36, 0000.
33. Gage, J. R.; Evans, D. A. Org. Synth. 1989, 57, 83.
34. (a) Evans, D. A.; Bartoli, J.; Shih, T. L. J. Am. Chem. Soc. 1981, 103, 2127.
35. (b) Evans, D. A.; Urpi, F.; Somer, T. C.; Clark, J. S.; Bilodeau, M. T. J. Am. Chem. Soc. 1990, 112, 8215.
36. (c) Evans, D. A.; Bilodeau, M. T.; Somer, T. C.; Clardy, J.; Cherry, D.; Kato, Y. J. Org. Chem. 1991, 56, 5750.
37. Oppolzer, W.; Cintas-Moreno, P.; Tamura, O. Cardinaux, F. Helv. Chim. Acta 1993, 76, 187.
38. Evans, D. A.; Britton, T. C.; Ellman, J. A. Tetrahedron Lett. 1982, 23, 3975.
39. 7a: oil; 1H NMR (400 MHi, CDCl3) S 0.88 (t, J=7.0 Hz, 3H), 1.17-1.43 (m, 22H), 1.53-1.63 (m,"2H), 2.05 (dd, J=17.7, 7 7 Hz, 1H), 2.76 (dd, J=17.8. 9.1 H/., IH), 3.95 (ddd, J=9 1, 7 5 6.4 Hz, IH), 4.39 (dd, J=V. 1. 3.7 Hz. IH), 4.44 (dd, J=V 3 7 8 Hz, IH), 4.62 (d, J=7.5 Hz. IH). 4.70 (ddd, J=9.5. 8.0, 6.4 Hz, IH), 5.36 (td, J=7.5, 3.8 Hz. IH). 7.13-7.40 (m, K)H); 13C NMR (KK)MHz, CDCl3)S 174.1, 170.4, 153.0, 138.9, 137.6, 129.2, 128.9, 128.7, 128.4. 128.1, 127.4,80.9,660,565 51 8 44.9, 34.9, 32.6. 31.8. 29.6. 29.4. 29.3. 29.1. 25.2, 22.6. 14.1; |o]D2(l -67.2° (c=().7. CHiCI2): Analysis calc'd for C14H4-JNO5: C, 74.56; H, 8.28; N, 2.56; found: C, 7476; H, X. 12; N, 2.57. 55* Yield.
40. Tb: mp 45-47 0C; 1H NMR (270 MHz, CDCl3) 8 0.88 (t, J=6.6 Hz, 3H), 1.23-1.64 (m, 8H). 2.06 (dd, J=17.9. 8.0 Hz, IH), 2.78 (dd, J=17.6, 9.5 Hz, IH), 3.95 (ddd, J=9.5, 8.0 6 4 Hz IH) 4.39 (dd, J=9.4, 2.7 Hz, IH), 4.44 (dd, J=9.4. 7.8 Hz, IH), 4.63 (d, J=7.3 Hz, IH), 4.7 (ddd, J=6.4, 6.4, 6.4 Hz. IH), 5.36 (td, J=7.2, 4.4 Hz, IH), 7.13-7.42 (m, K)H); 15C NMR (65 MHz, CDCl3)S 174.1, 170.4, 153.0. 138.9, 137.7, 129.1, 128.9, 128.6/ 128.4, 128.0, 127.3, 80.9, 66.0, 56.4, 51.8, 44.9, 34.8, 32.5, 31.3, 24.9, 22.4, 13.9; [a]D26 -82.1° (c=1.0, CH2Cl2); Analysis calc'd for C26H2NO5: C. 71.70: H, 6.71; N. 3.22; found: C, 71.52; H, 6.56; N, 2.97. 82'/! Yield.
41. 8a: mp 1120C(IiI. 109-111 0C); 1H NMR (4(K) MHz, CDCl3) S 0.88 (t, J=7.0 Hz, 3H), 1.21-1.51 (m, 22H), 1.72-1.81 (m, 2H), 2.82 (dd, J=17.7. 97 Hz, IH), 2.94 (dd, J=17.9, 8.4 Hz, IH), 3.10 (m, IH), 4.61 (td. J=7.5, 4.8 Hz. IH): 1CNMR(IOO MHz1CDCl3)S 175.8, 174.2,81.7,45.3.35.4,31.9,31.8,29.6, 29.5, 29.4, 29.3, 29.2, 25.2, 22.7. 14.1; |ct]D2<1 -42.9° (c=().55, CHCl3), (literature value for the (-)-enantiomer |a|rj26 -41 ° (c=0.5, CHCl3) Murta, M. M.; de Azevedo, M. B. M.; Greene, A. E. J. Org. Chem. 1993. 58, 7537). 85e* Yield.
42. Ia: mp 107-108 0C (lit. 108 0C); 1H NMR (400 MHz, CDCl3) S0.87(t, J=5.4 Hz, 3H), 1.25-1.34 (m, 22H), 1.38 (d, J=7.0 Hz, 3H), 1.67-1.84 (m, 2H), 2.70 (dd, J=I 1.3, 9.6 Hz, IH), 2.99 (m, IH), 4.47 (td, J=9.0, 4.4 Hz, IH); 13C NMR (100 MHz, CDCl3) 6 176.6, 175.7, 79.3, 53.8, 39.8, 34.9, 31.9, 29.6, 29.5, 29.4, 29.3, 25.3, 22.7, 14.5, 14.1; [ct]D26 -25.7° (c=0.6, CHCl3), [literature value for thé (-)-enantiomer [alo26 -26.0° (c=1.93, CHCl3) Mulzer, J.; Salimi, N.; Hartl, H. Tetrahedron: Asymmetry 1993, 4, 457]. 55% Yield.
43. 3) de Azevedo, M. B. M.; Murta, M. M.; Greene, A. E. J. Org. Chem. 1992, 57, 4567). 81% Yield.
44. 1H NMR. For an example of counterion dependent alkylation see: Kigoshi, H.; Imamura, Y.; Yoshikawa, K.; Niwa, H.; Yamada, K. Tetrahedron Lett. 1991, 32, 4541 and references cited therein.
45. Mulzer, J.; Salimi, N.; Hartl, H. Tetrahedron: Asymmetry 1993, 4, 457.
46. Takahata, H.; Uchida, Y.; Momose, T. J. Org. Chem. 1995, 60, 5628.