Synthesis of syn- and anti-3,5-Dihydroxy-6-heptenoates from 2-Deoxy-d-ribose: Intermediates for Polyols Synthesis

Abstract

Syntheses of all four diastereomers of syn- and anti-3,5-dihydroxy-6-heptenoate, proven versatile synthetic intermediates that are enantiomerically pure and functionally differentiated at both ends, have been developed.

Key words

1,3-diols synthesis - tetrahydro-2-furanylacetate - polyols - ring opening - 4-hydroxy-6-vinyltetrahydro-2H-2-pyranone

References

• 1 Naik SR. Harindran J. Nanda RK. Indian J. Chem., Sect. B  2001,  40:  1183 
• 2 Tsukamoto S. Ishibashi M. Sasaki T. Kobayashi J. J. Chem. Soc., Perkin Trans.1  1991,  3185 
• 3 Litaudon M. Hickford SJH. Lill RE. Lake RJ. Blunt JW. Munro MHG. J. Org. Chem.  1997,  62:  1868 
• 4 Pettit GR. Chicacz ZA. Gao F. Herald CL. Boyd MR. Schmidt JM. Hooper JNA. J. Org. Chem.  1993,  58:  1302 
• 5 Eh M. Kalesse M. Synlett  1995,  837 
• 6 Kumar A. Dittmer DC. J. Org. Chem.  1994,  59:  4760 
• 7 Harada T. Shintani T. Oku A. J. Am. Chem. Soc.  1995,  117:  12346 
• 8 Solladie G. Wilb N. Bauder C. Bonini C. Viggiani L. Chiummiento L. J. Org. Chem.  1999,  64:  5447 
• 9 Mohr P. Tetrahedron Lett.  1992,  33:  2455 
• 10 Scialdone MA. Johnson CR. Tetrahedron Lett.  1995,  36:  43 
• 11 Smith AB. Pitram SM. Org. Lett.  1999,  1:  2001 
• 12 Enders D. Hundertmark T. Tetrahedron Lett.  1999,  40:  4169 
• 13 Guindon Y. Zamboni R. Lau CK. Rokach J. Tetrahedron Lett.  1982,  23:  739 
• 14 Jewell CF. inventors; U.S. Patent  4625039.  ; Chem. Abstr. 1987, 106, 138255