Highly stereocontrolled access to a tetrahydroxy long chain base using anti-selective additions

Abstract

Complete diastereostereoselection was attained for the addition of acetylide and benzyloxymethyl anions to a chiral aldehyde and an imine derived from meso-tartaric acid, leading to a facile synthesis of (2S,3S,4R,5R,6Z)-2-amino-1,3,4,5-tetrahydroxyoctadecene as its pentaacetyl derivative in enantiomerically pure form.

References

1. Y. Hannun and R. M. Bell, Science, 1989, 243; C. Djerassi and W. K. Lam, Acc. Chem. Res., 1991, 24, 69; A. Olivera and S. Spiegel, Nature, 1993, 365, 557.
2. H. S. Garg, M. Sharma, D. S. Bhakuni, B. N. Paramanik and A. K. Bose, Tetrahedron Lett., 1992, 33, 1641; C. B. Rao and C. Satyanarayana, Indian J. Chem., Sect. B, 1994, 33B, 97.
3. G. Falsone, F. Cateni, F. Katusian, H. Wagner, O. Seligmann, G. Pellizer and F. Asaro, Z. Naturforsch, Teil B: Chem. Sci., 1993, 48, 1121; G. Falsone, F. Cateni, G. Visintin, V. Lucchini, H. Wagner and O. Seligmann, Farmaco, 1994, 49, 167.
4. (a) Y.-L. Li and Y.-L. Wu, Tetrahedron Lett., 1995, 36, 3875; (b) H. Yoda, T. Oguchi and K. Takabe, Tetrahedron: Asymmetry, 1996, 7, 2113.
5. For reviews, see, J. Jurczak and A. Golebiowski, Chem. Rev., 1989, 89, 149; Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon, Oxford, 1991, vol. 1 and references cited therein; A. Dondoni and D. Perrone, Aldrichim. Acta, 1997, 30, 35.
6. M. Shimizu, I. Wakioka and T. Fujisawa, Tetrahedron Lett., 1997, 38, 6027.
7. T. Fujisawa, M. Nagai, Y. Koike and M. Shimizu, J. Org. Chem., 1994, 59, 5865.
8. A. Dondoni and P. Merino, Synthesis, 1992, 196; P. Munier, A. Krusinski, D. Picq and D. Anker, Tetrahedron, 1995, 51, 1229.
9. For lipase-mediated kinetic resolution of this kind of diol, see, M. Pottie, V. der Eycken and M. Vandewalle, Tetrahedron: Asymmetry, 1991, 2, 329; H. J. Bestmann and L. Bauriegel, Tetrahedron Lett., 1995, 36, 853.
10. F. Tabusa, T. Yamada, K. Suzuki and T. Mukaiyama, Chem. Lett., 1984, 405.
11. D. A. Evans, G. L. Carroll and L. K. Truesdale, J. Org. Chem., 1974, 39, 914 and references cited therein.
12. E. J. Corey and T. M. Eckrich, Tetrahedron Lett., 1983, 24, 3163; W. C. Still, J. Am. Chem. Soc., 1978, 100, 1481.