RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00032269.xml
CC BY-ND-NC 4.0 · SynOpen 2019; 03(01): 36-45
DOI: 10.1055/s-0037-1611679
DOI: 10.1055/s-0037-1611679
paper
Stereoselective Synthesis of 4-O-Tosyltetrahydropyrans via Prins Cyclization Reaction of Enol Ethers
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.Weitere Informationen
Publikationsverlauf
Received: 20. Januar 2019
Accepted after revision: 05. Februar 2019
Publikationsdatum:
28. Februar 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
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1611679.
- 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