Stereoselective Synthesis of a Mevinic Acid Analogue [1]

Abstract

An efficient and versatile synthetic method for the stereoselective synthesis of a mevinic acid analogue is described. This approach uses a combination of a Cosford protocol with a catecholborane-mediated stereoselective reduction of acyclic β-hydroxy ketones to syn-1,3-diols, as key steps.

Key words

mevinic acid analogue - Cosford protocol - β-hydroxy ketones - catecholborane - syn-1,3-diols

1

IICT Communication No: 060910.

References

• 2 Alberts AW. Chen J. Kuron G. Hunt V. Huff J. Hoffman C. Rothrock J. Lopez M. Joshua H. Harris E. Patchett A. Monaghan R. Currie S. Stapley E. Albers-Schonberg G. Hensens O. Hirshfield J. Hoogsteen K. Liesch J. Springer J. Proc. Natl. Acad. Sci. USA  1980,  77:  3957 
• 3 Stokker GE. Hoffman WF. Alberta W. Cragon EJ. Deana AA. Gilfillan JL. Huff JW. Novello FC. Prugh JD. Smith RL. Willard AK. J. Med. Chem.  1985,  28:  347 
• For some examples of total synthesis, see:
• 4a Clive DLJ. Murthy KSK. Wee AGH. Prasad JS. da Silva GVJ. Majewski M. Anderson PC. Evans CF. Haugen RD. Heerze LD. Barrie JR. J. Am. Chem. Soc.  1990,  112:  3018 
• 4b Hagiwara H. Nakano T. Kon-no M. Uda H. J. Chem. Soc., Perkin Trans. 1  1995,  777 
• 4c Ghosh AK. Lei H. J. Org. Chem.  2000,  65:  4779 
• 4d Bouzbouz S. Cossy J. Tetrahedron Lett.  2000,  41:  3363 
• 4e Reddy PP. Yen K.-F. Uang B.-J. J. Org. Chem.  2002,  67:  1034 
• 4f Solladie G. Bauder C. Rossi L. J. Org. Chem.  1995,  60:  7774 
• 4g Aggarwal VK. Bae I. Lee H.-Y. Tetrahedron  2004,  60:  9725 
• 5 Bleicher L. Cosford NDP. Synlett  1995,  1115 
• 6 Evans DA. Hoveyda AH. J. Org. Chem.  1990,  55:  5190 
• 7 Yadav JS. Deshpande PK. Sharma GVM. Tetrahedron  1990,  46:  7033 
• 8 Evans DA. Rieger DL. Gage JR. Tetrahedron Lett.  1990,  31:  7099 
• 9 Johnson CR. Senanayake CH. J. Org. Chem.  1989,  54:  735 

1

IICT Communication No: 060910.