Simple synthesis of enantiomerically pure, protected cis-bicyclo[4.4.0]decane-1-carboxaldehyde derivatives from cyclohexanones by the 3-arenesulfonyloxazolidine route

Synthesis

Volumn , Issue 1, 1996, Pages 25-27

  Prien, Olaf ^a   Hoppe, Dieter ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

2 acyl 3 tosyl 1,3 oxazolidines; cis bicyclo 4.4.0 decanes; diastereoselective Robinson annulation

Indexed keywords

BICYCLO COMPOUND; DECALIN DERIVATIVE;

ARTICLE; DRUG PURITY; DRUG SYNTHESIS; ENANTIOMER; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0030062839     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-4170     Document Type: Article

References (24)

1. Review: Romo, D.; Meyers, A. I. Tetrahedron 1991, 47, 9503. For further examples, see: Snyder, L.; Meyers, A. I. J. Org. Chem. 1993, 58, 7507. Zhu, J.; Quirion, J.-C.; Husson, H.-P. J. Org. Chem. 1993, 58, 6451. Manganey, P.; Gosmini, R.; Raussou, S.; Commerçon, M.; Alexakis, A. J. Org. Chem. 1994, 59, 1877, and references cited therein.
2. Review: Romo, D.; Meyers, A. I. Tetrahedron 1991, 47, 9503. For further examples, see: Snyder, L.; Meyers, A. I. J. Org. Chem. 1993, 58, 7507. Zhu, J.; Quirion, J.-C.; Husson, H.-P. J. Org. Chem. 1993, 58, 6451. Manganey, P.; Gosmini, R.; Raussou, S.; Commerçon, M.; Alexakis, A. J. Org. Chem. 1994, 59, 1877, and references cited therein.
3. Review: Romo, D.; Meyers, A. I. Tetrahedron 1991, 47, 9503. For further examples, see: Snyder, L.; Meyers, A. I. J. Org. Chem. 1993, 58, 7507. Zhu, J.; Quirion, J.-C.; Husson, H.-P. J. Org. Chem. 1993, 58, 6451. Manganey, P.; Gosmini, R.; Raussou, S.; Commerçon, M.; Alexakis, A. J. Org. Chem. 1994, 59, 1877, and references cited therein.
4. Review: Romo, D.; Meyers, A. I. Tetrahedron 1991, 47, 9503. For further examples, see: Snyder, L.; Meyers, A. I. J. Org. Chem. 1993, 58, 7507. Zhu, J.; Quirion, J.-C.; Husson, H.-P. J. Org. Chem. 1993, 58, 6451. Manganey, P.; Gosmini, R.; Raussou, S.; Commerçon, M.; Alexakis, A. J. Org. Chem. 1994, 59, 1877, and references cited therein.
5. Harder, T.; Löhl, T.; Boite, M.; Wagner, K.; Hoppe, D. Tetrahedron Lett. 1994, 35, 7365.
6. Scolastico, C. Pure Appl. Chem. 1988, 60, 1689.
7. Poli, G.; Belvisi, L.; Manzoni, L.; Scolastico, C. J. Org. Chem. 1993, 58, 3165. Agami, C.; Couty, F.; Lequesne, C. Tetrahedron Lett. 1994, 35, 2063, and references cited therein.
8. Poli, G.; Belvisi, L.; Manzoni, L.; Scolastico, C. J. Org. Chem. 1993, 58, 3165. Agami, C.; Couty, F.; Lequesne, C. Tetrahedron Lett. 1994, 35, 2063, and references cited therein.
9. Hoppe, I.; Hoppe, D.; Wolff, C.; Egert, E.; Herbst, R. Angew. Chem. 1989, 101, 65; Angew. Chem. Int. Ed. Engl. 1989, 28, 67. Hoppe, I.; Hoffmann, H.; Gärtner, I.; Krettek, T.; Hoppe, D. Synthesis 1991, 1157.
10. Hoppe, I.; Hoppe, D.; Wolff, C.; Egert, E.; Herbst, R. Angew. Chem. 1989, 101, 65; Angew. Chem. Int. Ed. Engl. 1989, 28, 67. Hoppe, I.; Hoffmann, H.; Gärtner, I.; Krettek, T.; Hoppe, D. Synthesis 1991, 1157.
11. Hoppe, I.; Hoppe, D.; Wolff, C.; Egert, E.; Herbst, R. Angew. Chem. 1989, 101, 65; Angew. Chem. Int. Ed. Engl. 1989, 28, 67. Hoppe, I.; Hoffmann, H.; Gärtner, I.; Krettek, T.; Hoppe, D. Synthesis 1991, 1157.
12. Conde-Frieboes, K.; Hoppe, D. Synlett 1990, 99. Conde-Frieboes, K.; Hoppe, D. Tetrahedron 1992, 48, 6011.
13. Conde-Frieboes, K.; Hoppe, D. Synlett 1990, 99. Conde-Frieboes, K.; Hoppe, D. Tetrahedron 1992, 48, 6011.
14. Palazzi, C.; Poli, G.; Scolastico, C.; Villa, R. Tetrahedron Lett. 1990, 31, 4223.
15. Prien, O.; Hoffmann, H.; Conde-Frieboes, K.; Krettek, T.; Berger, B.; Wagner, K.; Bolte, M.; Hoppe, D. Synthesis 1994, 1313.
16. Review: Gawley, R. E. Synthesis 1976, 777, and references cited therein. Jung, M. E. Tetrahedron 1976, 32, 3. Little, R. D.; Masjedizadek, M. R.; Wallquist, O.; McLoughlin, J.J. Org. React. 1995, 47, 315.
17. Review: Gawley, R. E. Synthesis 1976, 777, and references cited therein. Jung, M. E. Tetrahedron 1976, 32, 3. Little, R. D.; Masjedizadek, M. R.; Wallquist, O.; McLoughlin, J.J. Org. React. 1995, 47, 315.
18. Review: Gawley, R. E. Synthesis 1976, 777, and references cited therein. Jung, M. E. Tetrahedron 1976, 32, 3. Little, R. D.; Masjedizadek, M. R.; Wallquist, O.; McLoughlin, J.J. Org. React. 1995, 47, 315.
19. Evans, D. A. In Asymmetric Synthesis; 2nd ed., Vol. 3B; Morisson, J. D., Ed.; Academic: Orlando, 1984; p 1.
20. Browne, L. M.; Klinck, R. E.; Stothers, J. B. Org. Magn. Reson. 1979, 12, 561.
21. Review: Hanson, J. R. Nat. Prod. Rep. 1992, 9, 139. See also: Eder, U.; Sauer, G.; Wiechert, R. Angew. Chem. 1971, 83, 492; Angew. Chem. Int. Ed. Engl. 1971, 10, 496. Ohrai, K.; Kondo, K.; Sodeoka, M.; Shibasaki, M. J. Am. Chem. Soc. 1994, 116, 11737.
22. Review: Hanson, J. R. Nat. Prod. Rep. 1992, 9, 139. See also: Eder, U.; Sauer, G.; Wiechert, R. Angew. Chem. 1971, 83, 492; Angew. Chem. Int. Ed. Engl. 1971, 10, 496. Ohrai, K.; Kondo, K.; Sodeoka, M.; Shibasaki, M. J. Am. Chem. Soc. 1994, 116, 11737.
23. Review: Hanson, J. R. Nat. Prod. Rep. 1992, 9, 139. See also: Eder, U.; Sauer, G.; Wiechert, R. Angew. Chem. 1971, 83, 492; Angew. Chem. Int. Ed. Engl. 1971, 10, 496. Ohrai, K.; Kondo, K.; Sodeoka, M.; Shibasaki, M. J. Am. Chem. Soc. 1994, 116, 11737.
24. Review: Hanson, J. R. Nat. Prod. Rep. 1992, 9, 139. See also: Eder, U.; Sauer, G.; Wiechert, R. Angew. Chem. 1971, 83, 492; Angew. Chem. Int. Ed. Engl. 1971, 10, 496. Ohrai, K.; Kondo, K.; Sodeoka, M.; Shibasaki, M. J. Am. Chem. Soc. 1994, 116, 11737.