A Concise Synthesis of (-)-(3S,6R)-3,6-Dihydroxy-10-methylundecanoic Acid Using a Cross-Metathesis Approach

Abstract

A new synthesis of (-)-(3S,6R)-3,6-dihydroxy-10-methylundecanoic acid, a β-hydroxy carboxylic acid, has been accomplished using a cross-metathesis reaction between two terminal olefin intermediates as the key step.

β-hydroxy acid - cross-metathesis - Jacobsen’s kinetic resolution - TMSI

References

1 Barreo AF. Herrador MM. Haidour A. Altarejos J. Arteaga P. Chahboun R. Tetrahedron Lett.  1995,  36:  2649 

2a Zhang X. Da S. Zhang C. Xie Z. Li Y. Tetrahedron Lett.  2006,  47:  507 

2b Pandey SK. Kumar P. Eur. J. Org. Chem.  2007,  369 

2c Xian-Shu Z. Shi-Jun D. Yang J. Hui-Zhi L. Zhi-Xiang X. Ying L. Chin. J. Chem.  2008,  26:  1315 

For recent examples of cross-metathesis reaction between two different allylic alcohols, see:

3a Shi Z. Harrison BA. Verdine GL. Org. Lett.  2003,  5:  633 

3b Zhu L. Mootoo DR. Org. Biomol. Chem.  2005,  3:  2750 

3c Crimmins MT. Zhang Y. Diaz FA. Org. Lett.  2006,  8:  2369 

3d Gupta P. Kumar P. Eur. J. Org. Chem.  2008,  1195 

4a Sabitha G. Fatima N. Gopal P. Reddy CN. Yadav JS. Tetrahedron: Asymmetry  2009,  20:  184 

4b Sabitha G. Bhaskar V. Reddy SSS. Helv. Chim. Acta  2009,  in press

5 Lescure P. Huet F. Synthesis  1987,  404 

6a Schaus SE. Brandes BD. Larrow JF. Tokunaga M. Hansen KB. Gould AE. Furrow ME. Jacobsen EN. J. Am. Chem. Soc.  2002,  124:  1307 

6b Louis JT. Nelson WL. J. Org. Chem.  1987,  52:  1309 

7 Alcaraz L. Harnett JJ. Mioskowski C. Martel JP. Legall T. Shin D.-S. Falck JR. Tetrahedron Lett.  1994,  35:  5449 

8 Sabitha G. Padmaja P. Sudhakar K. Yadav JS. Tetrahedron: Asymmetry  2009,  20:  1330 

9 Garegg PJ. Samuelson B. J. Chem. Soc., Chem. Commun.  1979,  978 

10 Kang S.-K. Kim S.-G. Cho D.-G. Jeon J.-H. Synth. Commun.  1993,  23:  681 

11a Connon SJ. Blechert S. Angew. Chem. Int. Ed.  2003,  42:  1900 

11b Chatterjee AK. Choi T.-L. Sanders DP. Grubbs RH. J. Am. Chem. Soc.  2003,  125:  11360