An efficient asymmetric synthesis of cascarillic acid

Synlett

Volumn , Issue 7, 2006, Pages 1119-1121

  Cheeseman, Matt ^a   Bull, Steven D ^a  

^a University of Bath Claverton Down   (United Kingdom)

Author keywords

Aldol; Cascarillic acid; Cyclopropane; Retro aldol; Temporary stereocentre

Indexed keywords

CASCARILLIC ACID; CYCLOPROPANE DERIVATIVE; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; CYCLOPROPANATION; DRUG STRUCTURE; DRUG SYNTHESIS;

EID: 33646568495     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-939690     Document Type: Article

References (25)

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3. For example: (a) Lactobacillic acid: Coxon, G. D.; Al Dulayymi, J. R.; Baird, M. S.; Knobl, S.; Roberts, E.; Minnikin, D. E. Tetrahedron: Asymmetry 2003, 14, 1211.
4. (b) Methyl dihydrosterculate: Stuart, L. J.; Buist, P. H. Tetrahedron: Asymmetry 2004, 15, 401.
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6. Cheeseman, M.; Feuillet, F. J. P.; Johnson, A. L.; Bull, S. D. Chem. Commun. 2005, 2372.
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8. Also see: (a) Dixon, D. J.; Scott, M. S.; Luckhurst, C. A. Synlett 2005, 2420.
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12. For a previous example where this methodology has been used for the oxidative C-1 homolgation of aldehydes to their corresponding acids see: Kametani, T.; Tsubuki, M.; Tatsuzaki, Y.; Honda, T. J. Chem. Soc., Perkin Trans. 1 1990, 639.
13. For a discussion of the potential benefits of using 5,5-dimethyl- oxazolidin-2-ones (SuperQuats) for asymmetric synthesis see: (a) Bull, S. D.; Davies, S. G.; Jones, S.; Sanganee, H. J. J. Chem. Soc., Perkin Trans. 1 1999, 387.
14. (b) Bull, S. D.; Davies, S. G.; Nicholson, R. L.; Sanganee, H. J.; Smith, A. D. Tetrahedron: Asymmetry 2000, 387.
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17. These conditions have been used previously for the preparation of racemic and chiral syn-aldols derived from N-acyl-oxazolidin-2-ones, see: (a) Ref. 4.
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20. (d) Feuillet, F. J. P.; Niyadurupola, D. G.; Green, R.; Cheeseman, M.; Bull, S. D. Synlett 2005, 1090.
21. 2′,3′) coupling constants of ≥7.0 Hz see: Evans, D. A.; Tedrow, J. S.; Shaw, J. T.; Downey, C. W. J. Am. Chem. Soc. 2002, 124, 392.
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23. For a discussion on the mechanism of directed cyclopropanation reactions of allylic alcohols, see: Nakamura, M.; Hirai, A.; Nakamura, E. J. Am. Chem. Soc. 2003, 125, 2341.
24. 2), 4.53 (1 H, dd, J = 10.0, 4.0 Hz, CHN), 4.36 (1 H, app. t, J = 6.5 Hz, CHOH), 4.09 (1 H, dd, J = 9.0,
25. +: 184.1458; found: 184.1458.