K. R. Prasad, P. Anbarasan / Tetrahedron: Asymmetry 16 (2005) 3951–3953
3953
3. (a) Vettel, S.; Lutz, C.; Diefenbach, G.; Haderlein, G.;
into (+)-exo-brevicomin {[a]D = +66.6 (c 0.3, Et2O),
lit.8 = +66.7; (c 1.40 Et2O)} in 72% yield.
Hammerschmidt, S.; Kuhling, K.; Mofid, M.-R.; Zim-
¨
mermann, T.; Knochel, P. Tetrahedron: Asymmetry 1997,
8, 779; (b) Macritchie, J. A.; Silcock, A.; Willis, C. L.
Tetrahedron: Asymmetry 1997, 8, 3895; (c) Agami, C.;
Mathieu, H. Tetrahedron Lett. 1998, 39, 3505; (d) McNe-
ill, A. H.; Thomas, E. J. Tetrahedron Lett. 1993, 34, 1669;
(e) Servi, S. Tetrahedron Lett. 1983, 24, 2023.
3. Conclusion
In summary, a high yielding approach for the synthesis
of a-hydroxy aldehydes tethered to an alkene was
accomplished by stereoselective reduction of a 1,4-di-
ketone derived from tartaric acid. The synthetic utility
of this methodology was illustrated by applying it to
the enantioselective synthesis of (+)-exo-brevicomin.
Synthesis of further functionalized hydroxy aldehdyes/
acids and their potential use as building blocks in oxy-
gen containing heterocycles is in progress.
4. Prasad, K. R.; Chandrakumar, A. Tetrahedron: Asymme-
try 2005, 16, 1897.
5. Nugiel, D. A.; Jakobs, K.; Worley, T.; Patel, M.;
Kaltenbach, R. F., III; Meyer, D. T.; Jadhav, P. K.; De
Lucca, G. V.; Smyser, T. E.; Klabe, R. M.; Bacheler, L. T.;
Rayner, M. M.; Seitz, S. P. J. Med. Chem. 1996, 39, 2156.
6. Sen, S. E.; Roach, S. L.; Boggs, J. K.; Ewing, G. J.;
Magrath, J. J. Org. Chem. 1997, 62, 6684.
7. Recent asymmetric synthesis of brevicomin: (a) Kumar,
D. N.; Rao, B. V. Tetrahedron Lett. 2004, 45, 2227; (b)
Raghavan, S.; Joseph, S. C. Tetrahedron Lett. 2003, 44,
8237; (c) de Sousa, A. L.; Resck, I. S. J. Braz. Chem. Soc.
2002, 13, 233; (d) Mayer, S. F.; Mang, H.; Steinreiber, A.;
Saf, R.; Faber, K. Can. J. Chem. 2002, 80, 362; (e) Gallos,
J. K.; Kyradjoglou, L. C.; Koftis, T. V. Heterocycles 2001,
55, 781; (f) Burke, S. D.; Muller, N.; Beudry, C. M. Org.
Lett. 1999, 1, 1827; (g) Hu, S.; Jayaraman, S.; Oehlsch-
lager, A. C. J. Org. Chem. 1999, 64, 2524; For a review on
the synthesis of pheromones see: (h) Mori, K. Eur. J. Org.
Chem. 1998, 1479.
Acknowledgements
We thank Department of Science and Technology
(DST), New Delhi, for funding of this project. P.A.
thanks IISc, Bangalore for a research fellowship.
References
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