Enzymatic resolution for an improved enantioselective synthesis of benzofuranyl derivatives: Precursors to a class of vitamin E related antioxidants

Tetrahedron Asymmetry

Volumn 8, Issue 1, 1997, Pages 45-55

  Ayers, Timothy A ^a   Schnettler, Richard A ^a   Marciniak, Gilbert ^a   Stewart, Kenneth T ^a   Mishra, Rajesh K ^a   Krysan, Damian J ^a   Bernas, Bradley R ^a   Bhardwaj, Poonam ^a   Fevig, Thomas L ^a  

^a SANOFI   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA TOCOPHEROL DERIVATIVE; ANTIOXIDANT; BENZOFURAN DERIVATIVE; TRIACYLGLYCEROL LIPASE;

ARTICLE; CANDIDA; DRUG PURIFICATION; DRUG SYNTHESIS; ENANTIOMER; ENZYME ACTIVITY; PRIORITY JOURNAL; REACTION ANALYSIS; TECHNIQUE;

EID: 0031023950     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(96)00494-6     Document Type: Article

References (14)

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2. For leading references see reference 1, footnotes 1-14.
3. Higgins, S. D.; Thomas, C. B. Conversion of Aromatic Ketones into α-Arylalkanoic Acids, Parts 1 and 2. Higgins, S. D.; Thomas, C. B. J. Chem. Soc., Perkin Trans. I 1983, 1483. Higgins, S. D.; Thomas, C. B. J. Chem. Soc., Perkin Trans, I 1982, 235.
4. Higgins, S. D.; Thomas, C. B. Conversion of Aromatic Ketones into α-Arylalkanoic Acids, Parts 1 and 2. Higgins, S. D.; Thomas, C. B. J. Chem. Soc., Perkin Trans. I 1983, 1483. Higgins, S. D.; Thomas, C. B. J. Chem. Soc., Perkin Trans, I 1982, 235.
5. Higgins, S. D.; Thomas, C. B. Conversion of Aromatic Ketones into α-Arylalkanoic Acids, Parts 1 and 2. Higgins, S. D.; Thomas, C. B. J. Chem. Soc., Perkin Trans. I 1983, 1483. Higgins, S. D.; Thomas, C. B. J. Chem. Soc., Perkin Trans, I 1982, 235.
6. Marciniak, G. Manuscript in preparation.
7. For another asymmetric approach to these compounds, see: Krysan, D. J. Tetrahedron Lett. 1996, 37, 1375.
8. Initial results in the rat models indicated that the R-2b was the most efficacious, so our work focused on the synthesis of this enantiomer.
9. Fries rearrangements conducted in situ and using previously prepared diester 3c were unsuccessful.
10. 3.
11. Wang, Y.-F.; Lalonde, J. J.; Momongan, M.; Bergbreiter, D. E.; Wong, C.-H. J. Am. Chem. Soc. 1988, 110, 7200.
12. The absolute configurations were established by comparison (HPLC and rotation) to authentic samples prepared by the previous route (ref. 4).
13. A similar amount of olefin 7 was generated when the corresponding bromide was used (ref. 4).
14. Henton, D. R.; McCreery, R. A.; Swenton, J. S. J. Org. Chem. 1980, 45, 369.