Chemoenzymatic synthesis of methyl (6S)-(-)-6,8-dihydroxyoctanoate: A precursor to (R)-(+)-α-lipoic acid

Synthesis

Volumn , Issue 5, 1996, Pages 594-596

  Santosh Laxmi, Y R ^a   Iyengar, D S ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

6,8 DIHYDROXYOCTANOIC ACID; OCTANOIC ACID DERIVATIVE; THIOCTIC ACID; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

ARTICLE; CANDIDA; CHIRALITY; DRUG SYNTHESIS; ENZYME ACTIVITY; REACTION ANALYSIS;

EID: 0029975304     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (22)

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11. Bullock, M. W.; Brockmann, J. A.; Patterson, E. L.; Pierce, J. V.; von Saltza, M. H.; Sanders, F.; Stokstad, E. L. R. J. Am. Chem. Soc. 1954, 76, 1828. Brookes, M. H.; Goldring, B. T.; Howes, D. A.; Hudson, A. T. J. Chem. Soc., Chem. Commun. 1983, 1051. Rao, A. V. R.; Gurjar, M. K.; Garyali, K.; Ravindranathan, T. Carhohydr. Res. 1986, 148, 51. Menon, R. B.; Kumar, M. A.; Ravindranathan, T. Tetrahedron Lett. 1987, 28, 5313. Elliot, J. D.; Steele, J.; Johnson, W. S. ibid. 1985, 26, 2535. Page, P. C. B.; Rayner, C. M.; Sutherland, I. O. J. Chem. Soc., Chem. Commun. 1986, 1408. Gopalan, A. S.; Jacobs, H. K. ibid. 1989, 30, 5705, and references cited in 1.
12. Bullock, M. W.; Brockmann, J. A.; Patterson, E. L.; Pierce, J. V.; von Saltza, M. H.; Sanders, F.; Stokstad, E. L. R. J. Am. Chem. Soc. 1954, 76, 1828. Brookes, M. H.; Goldring, B. T.; Howes, D. A.; Hudson, A. T. J. Chem. Soc., Chem. Commun. 1983, 1051. Rao, A. V. R.; Gurjar, M. K.; Garyali, K.; Ravindranathan, T. Carhohydr. Res. 1986, 148, 51. Menon, R. B.; Kumar, M. A.; Ravindranathan, T. Tetrahedron Lett. 1987, 28, 5313. Elliot, J. D.; Steele, J.; Johnson, W. S. ibid. 1985, 26, 2535. Page, P. C. B.; Rayner, C. M.; Sutherland, I. O. J. Chem. Soc., Chem. Commun. 1986, 1408. Gopalan, A. S.; Jacobs, H. K. ibid. 1989, 30, 5705, and references cited in 1.
13. Bullock, M. W.; Brockmann, J. A.; Patterson, E. L.; Pierce, J. V.; von Saltza, M. H.; Sanders, F.; Stokstad, E. L. R. J. Am. Chem. Soc. 1954, 76, 1828. Brookes, M. H.; Goldring, B. T.; Howes, D. A.; Hudson, A. T. J. Chem. Soc., Chem. Commun. 1983, 1051. Rao, A. V. R.; Gurjar, M. K.; Garyali, K.; Ravindranathan, T. Carhohydr. Res. 1986, 148, 51. Menon, R. B.; Kumar, M. A.; Ravindranathan, T. Tetrahedron Lett. 1987, 28, 5313. Elliot, J. D.; Steele, J.; Johnson, W. S. ibid. 1985, 26, 2535. Page, P. C. B.; Rayner, C. M.; Sutherland, I. O. J. Chem. Soc., Chem. Commun. 1986, 1408. Gopalan, A. S.; Jacobs, H. K. ibid. 1989, 30, 5705, and references cited in 1.
14. Bullock, M. W.; Brockmann, J. A.; Patterson, E. L.; Pierce, J. V.; von Saltza, M. H.; Sanders, F.; Stokstad, E. L. R. J. Am. Chem. Soc. 1954, 76, 1828. Brookes, M. H.; Goldring, B. T.; Howes, D. A.; Hudson, A. T. J. Chem. Soc., Chem. Commun. 1983, 1051. Rao, A. V. R.; Gurjar, M. K.; Garyali, K.; Ravindranathan, T. Carhohydr. Res. 1986, 148, 51. Menon, R. B.; Kumar, M. A.; Ravindranathan, T. Tetrahedron Lett. 1987, 28, 5313. Elliot, J. D.; Steele, J.; Johnson, W. S. ibid. 1985, 26, 2535. Page, P. C. B.; Rayner, C. M.; Sutherland, I. O. J. Chem. Soc., Chem. Commun. 1986, 1408. Gopalan, A. S.; Jacobs, H. K. ibid. 1989, 30, 5705, and references cited in 1.
15. Bullock, M. W.; Brockmann, J. A.; Patterson, E. L.; Pierce, J. V.; von Saltza, M. H.; Sanders, F.; Stokstad, E. L. R. J. Am. Chem. Soc. 1954, 76, 1828. Brookes, M. H.; Goldring, B. T.; Howes, D. A.; Hudson, A. T. J. Chem. Soc., Chem. Commun. 1983, 1051. Rao, A. V. R.; Gurjar, M. K.; Garyali, K.; Ravindranathan, T. Carhohydr. Res. 1986, 148, 51. Menon, R. B.; Kumar, M. A.; Ravindranathan, T. Tetrahedron Lett. 1987, 28, 5313. Elliot, J. D.; Steele, J.; Johnson, W. S. ibid. 1985, 26, 2535. Page, P. C. B.; Rayner, C. M.; Sutherland, I. O. J. Chem. Soc., Chem. Commun. 1986, 1408. Gopalan, A. S.; Jacobs, H. K. ibid. 1989, 30, 5705, and references cited in 1.
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17. Analogous reaction of trimethylsilyl iodide in acetone with (tetrahydro-2-furyl)methanol was first reported to give a protected 1,2-diol system: Amouroux, R.; Jatczak, M.; Chastreete, M. Bull. Soc. Chim. Fr. 1987, 505. Amouroux, R.; Jatczak, M.; Chastreete, M. Tetrahedron Lett. 1985, 26, 2315.
18. Analogous reaction of trimethylsilyl iodide in acetone with (tetrahydro-2-furyl)methanol was first reported to give a protected 1,2-diol system: Amouroux, R.; Jatczak, M.; Chastreete, M. Bull. Soc. Chim. Fr. 1987, 505. Amouroux, R.; Jatczak, M.; Chastreete, M. Tetrahedron Lett. 1985, 26, 2315.
19. The conversion of (6S)-6,8-dihydroxyoctanoate to (R)-(+)-lipoic acid involved inversion of configuration at C-6 as reported by White: White, R. H. J. Am. Chem. Soc. 1980, 102, 6605.
20. Dasaradhi, L.; Fadnavis, N. W.; Bhalerao, U. T. J. Chem. Soc., Chem. Commun. 1990, 729.
21. D - 5.8]. Ee of the alcohol was calculated based on the above value.
22. Barger, G.: Robinson, R.; Smith, L. R. J. Chem. Soc. 1937, 718.