Facile synthesis of β-hydroxy-γ-varelolactone via the ring opening reaction of β-trichloromethyl-β-propiolactone with ester enolates

Chemistry Letters

Volumn , Issue 8, 1997, Pages 765-766

  Shimizu, Makoto ^a   Ishii, Koichi ^a   Fujisawa, Tamotsu ^a  

^a MIE UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0010411688     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1997.765     Document Type: Article

References (22)

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8. a) G. Wess, K. Kesseler, E. Baader, W. Bartmann, A. Bergmann, H. Jendralla, K. Bock, G. Holzstein, H. Kleine, and M. Schniere, Tetrahedron Lett., 31, 2545 (1990).
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11. T. Fujisawa, T. Ito, K. Fujimoto, M. Shimizu, H. Wynberg, and E. G. J. Staring, Tetrahedron Lett., 38, 1593 (1997).
12. The enantiomeric purity of the recrystallized (5)-β-trichloromethyl-β-propiolactone from cyclohexane was determined to be >99% ee by GLC analysis using a chiral stationary column (Chiraldex G-TA, 20 m). Cf. H. Wynberg and E. G. J Staring, J. Am. Chem. Soc., 104, 166 (1982). H. Wynberg and E. G. J. Staring, J. Org. Chem., 50, 1977 (1985). H. Wynberg and E. G. J. Staring, J. Chem. Soc., Chem. Commun., 1984, 1181. P. E. F. Ketelaar, E. G. J. Staring, and H. Wynberg, Tetrahedron Lett., 26, 4665 (1985).
13. The enantiomeric purity of the recrystallized (5)-β-trichloromethyl-β-propiolactone from cyclohexane was determined to be >99% ee by GLC analysis using a chiral stationary column (Chiraldex G-TA, 20 m). Cf. H. Wynberg and E. G. J Staring, J. Am. Chem. Soc., 104, 166 (1982). H. Wynberg and E. G. J. Staring, J. Org. Chem., 50, 1977 (1985). H. Wynberg and E. G. J. Staring, J. Chem. Soc., Chem. Commun., 1984, 1181. P. E. F. Ketelaar, E. G. J. Staring, and H. Wynberg, Tetrahedron Lett., 26, 4665 (1985).
14. The enantiomeric purity of the recrystallized (5)-β-trichloromethyl-β-propiolactone from cyclohexane was determined to be >99% ee by GLC analysis using a chiral stationary column (Chiraldex G-TA, 20 m). Cf. H. Wynberg and E. G. J Staring, J. Am. Chem. Soc., 104, 166 (1982). H. Wynberg and E. G. J. Staring, J. Org. Chem., 50, 1977 (1985). H. Wynberg and E. G. J. Staring, J. Chem. Soc., Chem. Commun., 1984, 1181. P. E. F. Ketelaar, E. G. J. Staring, and H. Wynberg, Tetrahedron Lett., 26, 4665 (1985).
15. The enantiomeric purity of the recrystallized (5)-β-trichloromethyl-β-propiolactone from cyclohexane was determined to be >99% ee by GLC analysis using a chiral stationary column (Chiraldex G-TA, 20 m). Cf. H. Wynberg and E. G. J Staring, J. Am. Chem. Soc., 104, 166 (1982). H. Wynberg and E. G. J. Staring, J. Org. Chem., 50, 1977 (1985). H. Wynberg and E. G. J. Staring, J. Chem. Soc., Chem. Commun., 1984, 1181. P. E. F. Ketelaar, E. G. J. Staring, and H. Wynberg, Tetrahedron Lett., 26, 4665 (1985).
16. 4Cl. Usual work up and purification by silica gel chromatography gave the adduct as a colorless oil (1.35 g, 70%). The enantiomeric purity was determined to be >99% ee by GLC analysis (Chiraldex G-TA, 20 m).
17. K. Narasaka and F. C. Pai, Tetrahedron, 40, 2233 (1984).
18. -3) aqueous HCl (0.06 mL) to a toluene (9.0 mL) solution of the β,δ-dihydroxyacid 7 (35.8 mg, 0.14 mmol). Molecular sieves 4A (132 mg) was added to the solution, and the whole mixture was stirred at 50 °C for 24 h. Usual work-up gave lactone 8 (28.3 mg, 85%) as a sole product. Cf. J. E. Lynch, R. P. Volante, R. R. Wattley, and I. Shinkai, Tetrahedron Lett., 28, 1385 (1987).
19. 3).
20. C. E. Song, J. K. Lee, S. H. Lee, and S.-g. Lee, Tetrahedron: Asymm., 6, 1063 (1995).
21. 3). The enantiomeric purity was determined to be >99% ee by GLC (Chiraldex G-TA, 20 m).
22. Cf. Y. L. Yang, S. Manna, and J. R. Falck, J. Am. Chem. Soc., 106, 3811 (1984).