Enantioselective synthesis of (+)-shikimic acid and (+)-5-epi-shikimic acid by asymmetric Diels-Alder reaction of (S)-α-sulfinylacrylates

Tetrahedron Asymmetry

Volumn 8, Issue 10, 1997, Pages 1623-1631

  Adrio, Javier ^a   Carretero, Juan C ^a   Ruano, Jose L García ^a   Cabrejas, Luisa M Martín ^a  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

SHIKIMIC ACID; SHIKIMIC ACID DERIVATIVE;

ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS; ENANTIOMER; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; STEREOISOMERISM;

EID: 0030995556     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00151-1     Document Type: Article

References (36)

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22. During the preparation of this article, Evans and col. have just published a highly efficient enantioselective synthesis of (+)-shikimic acid based on the Diels-Alder reaction between acryloyl oxazolidinone and furan, catalyzed by a homochiral bis (4-tert-butyloxazoline) Cu(II) complex. See Evans, D. A.; Barnes, D. M. Tetrahedron Lett. 1997, 38, 57.
23. a) Campbell, M. M.; Kaye, A. D.; Sainbury, M.; Yavarzadeh, R. Tethahedron 1984, 40, 2461.
24. See also: b) Rajapaska, D.; Keay, B. A.; Rodrigo, R. Can. J. Chem. 1984, 62, 826.
25. The enantiopure (R) benzyl or t-butyl sulfinylacetates were prepared by Andersen reaction of the magnesium enolate of benzyl or t-butyl acetate with (S)-menthyl p-toluenesulfinate as it is described in ref. 3j (for the preparation of (S)-menthylp-toluenesulfinate, see: Solladie, G. Synthesis 1981, 185). As both enantiomers of menthol are commercially available, the sulfinylacetates of (S) configuration can be equally prepared from (R)-menthyl p-toluenesulfinate.
26. 2 is usually used as catalyst in the Diels-Alder reaction of acrylates with furan (see ref. 6a).
27. 4 is by far the most effective catalyst for the cycloadditions of sulfinyl maleates and sulfinyl trialkoxycarbonyl ethenes (see refs 3d and 3j).
28. 2.
29. 3, rt) of endo-4B to give bromolactone 14. (formula presented)
30. For other precedent of formation of bis-adducts in the Diels-Alder reaction with furan at high pressures, see: Sera, A.; Ohara, M.; Kubo, T.; Itoh, K.; Yamada, H.; Mikata, Y.; Kaneko, C.; Katagiri, N. J. Org. Chem. 1988, 53, 5460.
31. Arai, Y.; Matsui, M.; Koizumi, T. J. Chem. Soc. Perkin Trans. I, 1990, 1233.
32. This moderate overall yield is mainly due to the competitive formation of t-butyl benzoate as a result of the aromatization of 6 and 7. Very similar yields have been reported for related cyclohexadienols (see ref. 6).
33. 2O); Pawlak, J. L.; Berchtold, G. A. J. Org. Chem. 1987, 52, 1765. The difference between the experimental and literature values of optical rotation can be explained as a consequence of the concentration of the samples.
34. 20 lit.=-57.6 (c 0.8, MeOH); Jiang, S.; Mekki, B.; Singh, G.; Wightman, R.H. Tetrahedron Lett. 1994, 35, 5505.
35. Although this publication describes the enantioselective synthesis of (+)-shikimic acid, the non natural enantiomer, the synthesis of the natural (-)-enantiomer and its corresponding (-)-C-5 epimer would be accomplished in an identical way starting from (R) t-butyl α-p-tolylsulfinylacrylate instead of its (S)-enantiomer. To this effect it is important to note that both enantiomeric dienophiles are equally available (see ref. 7).
36. Solladié, G.; Mioskowski, C. Tetrahedron Lett. 1975, 3341.