Stereoselective Synthesis of 4-O-Tosyltetrahydropyrans via Prins Cyclization Reaction of Enol Ethers

Abstract

Intramolecular cyclization of enol ethers mediated by para-toluenesulfonic acid leads to substituted tetrahydropyrans in good to moderate yields. The reaction is diastereoselective.

Key words

tosyl tetrahydropyrans - Prins reaction - enol ether - cyclization - heterocycle

• References

• 1a Polyether Antibiotics, Vols. I and II . Westly JW. Dekker; New York: 1983
• 1b Faulkner DJ. Nat. Prod. Rep. 2002; 19: 1
• 1c Angle SR, El-Said NA. J. Am. Chem. Soc. 1999; 121: 10211
• 1d Huang H, Panek JS. J. Am. Chem. Soc. 2000; 122: 9836
• 1e Yoshimitsu T, Makino T, Nagaoka H. J. Org. Chem. 2004; 69: 1993
• 1f Class YJ, DeShong P. Chem. Rev. 1995; 95: 1843
• 1g Norcross RD, Paterson I. Chem. Rev. 1995; 95: 2041
• 1h Nasir NM, Ermanis K, Clarke PA. Org. Biomol. Chem. 2014; 12: 3323
• 1i Cons BD, Bunt AJ, Bailey CD, Willis CL. Org. Lett. 2013; 15: 2046
• 2 Wright AE, Botelho JC, Guzman E, Harmody D, Linley P, McCarthy PJ, Pitts TP, Pomponi SA, Reed JK. J. Nat. Prod. 2007; 70: 412
• 3 Juch M, Rüedi P. Helv. Chim. Acta 1997; 80: 436
• 4a Kunze B, Jansen R, Sasse F, Hofle G, Reichenbach H. J. Antibiot. 1998; 51: 1075
• 4b Kwon HJ, Kim DH, Shik JS, Ahn JW. J. Microbiol. Biotechnol. 2002; 12: 702
• 5 Tadpetch K, Rychnovsky SD. Org. Lett. 2008; 10: 4839
• 6a Bondalapati S, Reddy UC, Kundu DS, Saikia AK. J. Fluorine Chem. 2010; 113: 320
• 6b Yadav JS, Reddy BV. S, Anusha B, Reddy UV. S, Reddy VV. B. Tetrahedron Lett. 2010; 51: 2872
• 6c Launay GG, Slawin AM. Z, O’Hagan D. Beilstein J. Org. Chem. 2010; 6: 41
• 6d Yang J, Viswanathan GS, Li C.-J. Tetrahedron Lett. 1999; 40: 1627
• 6e Miranda PO, Carballo RM, Martín VS, Padrón JI. Org. Lett. 2009; 11: 357
• 7a Yang X.-F, Wang M, Zhang Y, Li C.-J. Synlett 2005; 12
• 7b Reddy UC, Bondalapati S, Saikia AK. Eur. J. Org. Chem. 2009; 25
• 7c Reddy UC, Raju BR, Kumar EK. P, Saikia AK. J. Org. Chem. 2008; 73: 1628
• 7d Reddy BV. S, Chaya DN, Yadav JS, Chatterjee D, Kunwar AC. Tetrahedron Lett. 2011; 52: 2961
• 8 Ahmed N, Konduru NK. Beilstein J. Org. Chem. 2012; 8: 177
• 9 Yadav JS, Reddy BV. S, Kumar GG. K. S. N, Reddy GM. Tetrahedron Lett. 2007; 48: 4903
• 10 Hart DJ, Bennett CE. Org. Lett. 2003; 5: 1499
• 11a Sultana S, Indukuri K, Deka MJ, Saikia AK. J. Org. Chem. 2013; 78: 12182
• 11b Gogoi P, Das VK, Saikia AK. J. Org. Chem. 2014; 79: 8592
• 12 Saikia AK, Indukuri K, Das J. Org. Biomol. Chem. 2014; 12: 7026
• 13 Sabitha G, Reddy KB, Reddy GS. K. K, Fatima N, Yadav JS. Synlett 2005; 2347
• 14a Feuer H, Nielsen AT. J. Am. Chem. Soc. 1962; 84: 688
• 14b McMurry JE, Melton J. J. Org. Chem. 1973; 38: 4367