A convenient synthesis of (-)-methyl epijasmonate

Synthetic Communications

Volumn 27, Issue 17, 1997, Pages 2931-2941

  U, Jong Sun ^a   Park, Hyun Seok ^a   Gupta, Sandhya ^a   Cha, Jin Kun ^a  

^a UNIVERSITY OF ALABAMA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPENTANONE DERIVATIVE; METHYL EPIJASMONATE; UNCLASSIFIED DRUG;

ARTICLE; DEGRADATION; ENANTIOMER; HYDROGENATION; SYNTHESIS;

EID: 1842404123     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919708004999     Document Type: Article

References (31)

1. For previous syntheses of (±)-1, see: (a) Tanaka, H.; Torii, S. J. Org. Chem. 1975, 40, 462. (b) Stevens, R. V.; Hrib, N. Tetrahedron Lett. 1981, 22, 4791. (c) Seto, H.; Yoshioka, H. Chem. Lett. 1990, 1797. (d) Kitahara, T.; Warita, Y.; Abe, M.; Seya, M.; Takagi, Y.; Mori, K. Agric. Biol. Chem. 1991, 55, 1013. (e) Crombie, L.; Mistry, K. M. J. Chem. Soc., Perkin 1 1991, 1981. (f) Stork, G.; Ouerfelli, O. New. J. Chem. 1992, 16, 95. (g) Sarkar, T. K.; Ghorai, B. K.; Banerji, A. Tetrahedron Lett. 1994, 35, 6907.
2. For previous syntheses of (±)-1, see: (a) Tanaka, H.; Torii, S. J. Org. Chem. 1975, 40, 462. (b) Stevens, R. V.; Hrib, N. Tetrahedron Lett. 1981, 22, 4791. (c) Seto, H.; Yoshioka, H. Chem. Lett. 1990, 1797. (d) Kitahara, T.; Warita, Y.; Abe, M.; Seya, M.; Takagi, Y.; Mori, K. Agric. Biol. Chem. 1991, 55, 1013. (e) Crombie, L.; Mistry, K. M. J. Chem. Soc., Perkin 1 1991, 1981. (f) Stork, G.; Ouerfelli, O. New. J. Chem. 1992, 16, 95. (g) Sarkar, T. K.; Ghorai, B. K.; Banerji, A. Tetrahedron Lett. 1994, 35, 6907.
3. For previous syntheses of (±)-1, see: (a) Tanaka, H.; Torii, S. J. Org. Chem. 1975, 40, 462. (b) Stevens, R. V.; Hrib, N. Tetrahedron Lett. 1981, 22, 4791. (c) Seto, H.; Yoshioka, H. Chem. Lett. 1990, 1797. (d) Kitahara, T.; Warita, Y.; Abe, M.; Seya, M.; Takagi, Y.; Mori, K. Agric. Biol. Chem. 1991, 55, 1013. (e) Crombie, L.; Mistry, K. M. J. Chem. Soc., Perkin 1 1991, 1981. (f) Stork, G.; Ouerfelli, O. New. J. Chem. 1992, 16, 95. (g) Sarkar, T. K.; Ghorai, B. K.; Banerji, A. Tetrahedron Lett. 1994, 35, 6907.
4. For previous syntheses of (±)-1, see: (a) Tanaka, H.; Torii, S. J. Org. Chem. 1975, 40, 462. (b) Stevens, R. V.; Hrib, N. Tetrahedron Lett. 1981, 22, 4791. (c) Seto, H.; Yoshioka, H. Chem. Lett. 1990, 1797. (d) Kitahara, T.; Warita, Y.; Abe, M.; Seya, M.; Takagi, Y.; Mori, K. Agric. Biol. Chem. 1991, 55, 1013. (e) Crombie, L.; Mistry, K. M. J. Chem. Soc., Perkin 1 1991, 1981. (f) Stork, G.; Ouerfelli, O. New. J. Chem. 1992, 16, 95. (g) Sarkar, T. K.; Ghorai, B. K.; Banerji, A. Tetrahedron Lett. 1994, 35, 6907.
5. For previous syntheses of (±)-1, see: (a) Tanaka, H.; Torii, S. J. Org. Chem. 1975, 40, 462. (b) Stevens, R. V.; Hrib, N. Tetrahedron Lett. 1981, 22, 4791. (c) Seto, H.; Yoshioka, H. Chem. Lett. 1990, 1797. (d) Kitahara, T.; Warita, Y.; Abe, M.; Seya, M.; Takagi, Y.; Mori, K. Agric. Biol. Chem. 1991, 55, 1013. (e) Crombie, L.; Mistry, K. M. J. Chem. Soc., Perkin 1 1991, 1981. (f) Stork, G.; Ouerfelli, O. New. J. Chem. 1992, 16, 95. (g) Sarkar, T. K.; Ghorai, B. K.; Banerji, A. Tetrahedron Lett. 1994, 35, 6907.
6. For previous syntheses of (±)-1, see: (a) Tanaka, H.; Torii, S. J. Org. Chem. 1975, 40, 462. (b) Stevens, R. V.; Hrib, N. Tetrahedron Lett. 1981, 22, 4791. (c) Seto, H.; Yoshioka, H. Chem. Lett. 1990, 1797. (d) Kitahara, T.; Warita, Y.; Abe, M.; Seya, M.; Takagi, Y.; Mori, K. Agric. Biol. Chem. 1991, 55, 1013. (e) Crombie, L.; Mistry, K. M. J. Chem. Soc., Perkin 1 1991, 1981. (f) Stork, G.; Ouerfelli, O. New. J. Chem. 1992, 16, 95. (g) Sarkar, T. K.; Ghorai, B. K.; Banerji, A. Tetrahedron Lett. 1994, 35, 6907.
7. For previous syntheses of (±)-1, see: (a) Tanaka, H.; Torii, S. J. Org. Chem. 1975, 40, 462. (b) Stevens, R. V.; Hrib, N. Tetrahedron Lett. 1981, 22, 4791. (c) Seto, H.; Yoshioka, H. Chem. Lett. 1990, 1797. (d) Kitahara, T.; Warita, Y.; Abe, M.; Seya, M.; Takagi, Y.; Mori, K. Agric. Biol. Chem. 1991, 55, 1013. (e) Crombie, L.; Mistry, K. M. J. Chem. Soc., Perkin 1 1991, 1981. (f) Stork, G.; Ouerfelli, O. New. J. Chem. 1992, 16, 95. (g) Sarkar, T. K.; Ghorai, B. K.; Banerji, A. Tetrahedron Lett. 1994, 35, 6907.
8. For previous syntheses of (+)-1, see: (a) Helmchen, G.; Goeke, A.; Lauer, G.; Urmann, M.; Fries, J. Angew. Chem., Int. Ed. Engl. 1990, 29, 1024. (b) Weinges, K.; Lernhardt, U. Liebigs Ann. Chem. 1990, 751. (c) Kitahara, T.; Nishi, T.; Mori, K. Tetrahedron 1991, 47, 6999. (d) Stadtmüller, H.; Knochel, P. Synlett 1995, 463. Cf. (e) Kitahara, T.; Inoue, M.; Tamogami, S.; Kaiser, R. Tetrahedron 1996, 52, 1487.
9. For previous syntheses of (+)-1, see: (a) Helmchen, G.; Goeke, A.; Lauer, G.; Urmann, M.; Fries, J. Angew. Chem., Int. Ed. Engl. 1990, 29, 1024. (b) Weinges, K.; Lernhardt, U. Liebigs Ann. Chem. 1990, 751. (c) Kitahara, T.; Nishi, T.; Mori, K. Tetrahedron 1991, 47, 6999. (d) Stadtmüller, H.; Knochel, P. Synlett 1995, 463. Cf. (e) Kitahara, T.; Inoue, M.; Tamogami, S.; Kaiser, R. Tetrahedron 1996, 52, 1487.
10. For previous syntheses of (+)-1, see: (a) Helmchen, G.; Goeke, A.; Lauer, G.; Urmann, M.; Fries, J. Angew. Chem., Int. Ed. Engl. 1990, 29, 1024. (b) Weinges, K.; Lernhardt, U. Liebigs Ann. Chem. 1990, 751. (c) Kitahara, T.; Nishi, T.; Mori, K. Tetrahedron 1991, 47, 6999. (d) Stadtmüller, H.; Knochel, P. Synlett 1995, 463. Cf. (e) Kitahara, T.; Inoue, M.; Tamogami, S.; Kaiser, R. Tetrahedron 1996, 52, 1487.
11. For previous syntheses of (+)-1, see: (a) Helmchen, G.; Goeke, A.; Lauer, G.; Urmann, M.; Fries, J. Angew. Chem., Int. Ed. Engl. 1990, 29, 1024. (b) Weinges, K.; Lernhardt, U. Liebigs Ann. Chem. 1990, 751. (c) Kitahara, T.; Nishi, T.; Mori, K. Tetrahedron 1991, 47, 6999. (d) Stadtmüller, H.; Knochel, P. Synlett 1995, 463. Cf. (e) Kitahara, T.; Inoue, M.; Tamogami, S.; Kaiser, R. Tetrahedron 1996, 52, 1487.
12. For previous syntheses of (+)-1, see: (a) Helmchen, G.; Goeke, A.; Lauer, G.; Urmann, M.; Fries, J. Angew. Chem., Int. Ed. Engl. 1990, 29, 1024. (b) Weinges, K.; Lernhardt, U. Liebigs Ann. Chem. 1990, 751. (c) Kitahara, T.; Nishi, T.; Mori, K. Tetrahedron 1991, 47, 6999. (d) Stadtmüller, H.; Knochel, P. Synlett 1995, 463. Cf. (e) Kitahara, T.; Inoue, M.; Tamogami, S.; Kaiser, R. Tetrahedron 1996, 52, 1487.
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21. Moreover, the preparation of the unnatural jasmonoid (-)-1 would be useful in clarifying conflicting reports on an interesting structure-activity relationship: see ref 2c and references cited therein.
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23. (b) Hernández, R.; Melián, D.; Suárez, E. Synthesis 1992, 653.
24. For oxidative extrusion of the alkyl iodides, see also: Lee, J.; Oh, J.; Jin, S.-j.; Choi, J.-R.; Atwood, J. L.; Cha, J. K. J. Org. Chem. 1994, 59, 6955 and references cited therein.
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30. For a description of general experimental procedures, see: Jin, S.-j.; Choi, J.-R.; Oh, J.; Lee, D.; Cha, J. K. J. Am. Chem. Soc. 1995, 117, 10914.
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