Oxazoline N-oxide-mediated [2+3] cycloadditions. Application to a synthesis of (-)-tetrahydrolipstatin

Organic Letters

Volumn 1, Issue 5, 1999, Pages 753-755

  Dirat, O ^a   Kouklovsky, C ^a   Langlois, Yves ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000143188     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990734k     Document Type: Article

References (15)

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2. Total syntheses: (a) Paterson, I.; Doughty, V. A. Tetrahedron Lett. 1999, 40, 393.
3. (b) Fleming, I.; Lawrence, N. J. J. Chem. Soc., Perkin Trans. 1 1998, 2679.
4. (c) For reviews on β-lactone synthesis, see: Pommier, A.; Pons, J.-M. Synthesis 1995, 729. Yang, H. W.; Romo, D. Tetrahedron 1999, 55, 6403 (and references therein).
5. (c) For reviews on β-lactone synthesis, see: Pommier, A.; Pons, J.-M. Synthesis 1995, 729. Yang, H. W.; Romo, D. Tetrahedron 1999, 55, 6403 (and references therein).
6. For a review, see: (a) Langlois, Y. Curr. Org. Chem. 1998, 2, 1.
7. (b) Kouklovsky, C.; Dirat, O.; Berranger, T.; Langlois, Y.; Tran Huu Dau, M.-E.; Riche, C. J. Org. Chem. 1998, 63, 5123.
8. (c) Dirat, O.; Kouklovsky, C.; Langlois, Y. J. Org. Chem. 1998, 63, 6634.
9. 1H NMR analysis of the corresponding O-acetylmandelate ester of alcohol 3; see: Hanessian, S.; Tehim, A.; Chen, P. J. Org. Chem. 1993, 58, 7768.
10. The same compound has been described under the racemic form: Oblin, L.; Parrain, J.-L.; Rajzmann, M.; Pons, J.-M. J. Chem. Soc., Chem. Commun. 1998, 1619.
11. Direct reduction of the ester 8 with DIBAH gave aldehyde 9 in 76% yield.
12. Under these conditions, the Wittig resulting compound 11 was obtained in 80% yield as a crude product. As degradation occurred during purification, crude 11 was taken in the next reaction.
13. Kraus, G. A.; Tashner, M. J. J. Org. Chem. 1980, 45, 1175.
14. Barbier, P.; Schneider, F. Helv. Chim. Acta 1987, 70, 196.
15. 13C NMR spectra, HRMS, and optical rotation.