CC BY-ND-NC 4.0 · SynOpen 2019; 03(01): 36-45
DOI: 10.1055/s-0037-1611679
paper
Copyright with the author

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

Sujit Sarkar
,
Namita Devi
,
Bikoshita Porashar
,
Santu Ruidas
,
Anil K Saikia*
This work is supported by the Department of Science and Technology (DST), New Delhi (Grant No. EMR/2016/006411), and CoE, MHRD, Government of India.
Further Information

Publication History

Received: 20 January 2019

Accepted after revision: 05 February 2019

Publication Date:
28 February 2019 (online)

Abstract

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

Supporting Information

 
  • 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