An alternative enantioselective synthesis of (+)-tricyclodecadienone

Tetrahedron Letters

Volumn 38, Issue 14, 1997, Pages 2527-2530

  Knol, Joop ^a   Feringa, Ben L ^a  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

HETEROCYCLIC KETONE; MENTHOL; TRICYCLODECADIENONE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; DRUG SYNTHESIS; ENANTIOMER; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030900920     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00392-4     Document Type: Article

References (31)

1. For recent applications of enantiomerically pure tricyclodecadienone 1: (a) Garland, R.B.; Miyano, M.; Pireh, D.; Clare, M.; Finnegan, P.M.; Swenton, L. J. Org. Chem. 1990, 55, 5854.
2. (b) Klunder, A.J.H.; Zwanenburg, B.; Liu, Z.-Y. Tetrahedron Lett. 1991, 32, 3131.
3. (c) Ogasawara, K. Pure Appl. Chem. 1994, 66, 2119 and references cited.
4. (d) Zhu, J.; Yang, J.-Y.; Klunder, A.J.H.; Liu, Z.-Y.; Zwanenburg, B. Tetrahedron 1995, 51, 5847 and references cited.
5. (e) Tanaka, K.; Ogasawara, K. Synthesis, 1996, 219.
6. Syntheses of tricyclodecadienone 1 via enzymatic resolutions: (a) Klunder, A.J.H.; Huizinga, W.B.; Hulshof, A.J.M.; Zwanenburg, B. Tetrahedron Lett. 1986, 27, 2543.
7. (b) Takano, S.; Inomata, K.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1989, 271.
8. (c) Takano, S.; Moriya, M.; Tanaka, K.; Ogasawara, K. Synthesis 1994, 687.
9. (d) Tanaka, K.; Ogasawara, K. Synthesis 1995. 1237.
10. (e) Sugahara, T.; Kuroyanagi, Y.; Ogasawara, K. Synthesis 1996, 1101.
11. Other methodologies: (f) Childs, B.J.; Edwards, G.L. Tetrahedron Lett. 1993, 34, 5341.
12. (g) Bakkeren, F.J.A.D.; Ramesh, N.G.; De Groot, D.; Klunder, A.J.H.; Zwanenburg, B. Tetrahedron Lett. 1996, 37, 8003.
13. (a) De Jong, J.C.; Feringa, B.L. J. Org. Chem. 1988, 53, 1125.
14. (b) De Jong, J.C.; Van Bolhuis, F.; Feringa, B.L. Tetrahedron: Asymmetry 1991, 2, 1247.
15. Martel, J.; Tessier, J., Demoute, J.P. Eur. Pat. Appl. 23454, 1981; Chem. Abstr. 1981, 95, 24788. For the synthesis of 5R- and 5S-(menthyloxy)-2(5H)-furanone involving a second order asymmetric transformation see: Feringa, B.L.; De Lange, B.; De Jong, J.C. J. Org. Chem. 1989, 54, 2471.
16. Martel, J.; Tessier, J., Demoute, J.P. Eur. Pat. Appl. 23454, 1981; Chem. Abstr. 1981, 95, 24788. For the synthesis of 5R- and 5S-(menthyloxy)-2(5H)-furanone involving a second order asymmetric transformation see: Feringa, B.L.; De Lange, B.; De Jong, J.C. J. Org. Chem. 1989, 54, 2471.
17. Recent applications of 5R-(l-menthyloxy)-2(5H)-furanone: (a) Feringa, B.L.; De Jong, J.C. Bull. Chem. Soc. Chim. Belg. 1992, 101, 627.
18. (b) Feringa, B.L.; de Lange, B.; Jansen, J.F.G.A.; De Jong, J.C.; Lubben, M.; Faber, W.; Schudde, E.P. Pure Appl. Chem. 1992, 64, 1865.
19. (c) Van Oeveren, A.; Jansen, J.F.G.A.; Feringa, B.L. J. Org. Chem. 1994, 59, 5999.
20. (d) Van Oeveren, A.; Feringa, B.L. J. Org. Chem. 1996, 61, 2920.
21. Other examples of WHE cyclizations: (a) Henrick, C.A.; Böhme, E.; Edwards, J.A.; Fried, J.H. J. Am. Chem. Soc. 1968, 90, 5926.
22. (b) Borcherding, D.R.; Scholtz, S.A.; Borchardt, R.T. J. Org. Chem. 1987, 52, 5457.
23. (c) Mikolajczyk, M.; Mikina, M. J. Org. Chem. 1994, 59, 6760 and references cited.
24. (d) Sundermann, B.; Scharf, H.-D. Tetrahedron: Asymmetry 1996, 7, 1995.
25. (e) Mikolajczyk, M.; Mikina, M.; Wieczorek, M.W.; Blaszczyk, J. Angew. Chem. Int. Ed. Engl. 1996, 35, 1560.
26. 4P: 254.071. Found: 254.071.
27. The amount of Knoevenagel product was increased when reaction mixtures were left at room temperature for prolonged periods. This illustrates that the dehydration process leading to 6 is a relatively slow process.
28. 1H-NMR. Filtration over silica gel (diethyl ether) afforded pure (+)-1 (57-62%, based on recovered 6) as a white solid.
29. 28 +138.4 ° (c = 0.81, MeOH); e.e. > 99% according to HPLC analysis (Daicel OB, eluent hexane/iPrOH 9 1 ).
30. Additionally, lithium salts might also function as weak lewis acids for the activation of 2.
31. Typical experimental procedure: To a stirred and cooled (-78 °C) solution of dimethyl methylphosphonate (595 mg, 4.8 mmol) and anhydrous lithium bromide (417 mg, 4.8 mmol) in dry THF (20 mL) was added n-butyllithium (3 mL of a 1.6 M solution in hexanes, 4.8 mmol) over a period of ± 2 min. The resulting clear solution was stirred at -78 °C for 30 min after which a solution of 2 (1.45 g, 4.8 mmol) in dry THF (5 mL) was added at once. Stirring was continued for an additional period of 2 h at -78 °C and the mixture was allowed to reach room temperature in 3 1 2 h. After addition of water (10 mL) and evaporation of THF in vacuo the resulting aqueous residue was continuously extracted with hexane (100 mL) for 20 h. Evaporation of the solvent in vacuo yielded a slightly yellow oil which was purified by column chromatography (see ) to yield pure l-(-)-menthol (661 mg, 93%) and (+)-1 (459 mg. 69%).