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Synlett 2005(12): 1912-1916
DOI: 10.1055/s-2005-871929
DOI: 10.1055/s-2005-871929
LETTER
© Georg Thieme Verlag Stuttgart · New York2,4-Diaryltetrahydropyran Formation by the Prins Cyclization and Its Application towards the Synthesis of Epicalyxin F and Calyxin I
Weitere Informationen
Received
19 April 2005
Publikationsdatum:
07. Juli 2005 (online)
Publikationsverlauf
Publikationsdatum:
07. Juli 2005 (online)

Abstract
A three-component Prins-Friedel-Crafts reaction was developed to synthesize 4-aryl tetrahydropyran derivatives. The methodology was applied towards the synthesis of calyxin I in ionic liquid.
Key words
Prins cyclization - Friedel-Crafts reaction - ionic liquids - tetrahydropyrans
- 1a
Wesley JW. Ann. Rep. Med. Chem. 1975, 10: 246 - 1b
Pressman BC. Ann. Rev. Biochem. 1976, 45: 501 - 1c
Ohuchida S.Hamanaka N.Hayashi M. Tetrahedron 1983, 39: 4203 - 1d
Kale VN.Clive DLJ. J. Org. Chem. 1984, 49: 1554 - 1e
Bhagwat SS.Hamann PR.Still WC.Buntiny S.Fitzpatric FA. Nature (London) 1985, 315: 511 - 2a
Ziegler FE. Acc. Chem. Res. 1977, 10: 227 - 2b
Collum DB.McDonald JH.Still WC. J. Am. Chem. Soc. 1980, 102: 2117 - 2c
Schmidt RR. Acc. Chem. Res. 1986, 19: 250 - 2d
Nicolaou KC.Prasad CVC.Somers CK. J. Am. Chem. Soc. 1989, 111: 5330 - 2e
Padwa A. Acc. Chem. Res. 1991, 24: 22 - 2f
Mori Y. Chem.-Eur. J. 1997, 3: 849 - 2g
Grubbs RH.Chang S. Tetrahedron 1998, 54: 4413 - For reviews of the Prins reaction, see:
- 3a
Arundale E.Mikeska LA. Chem. Rev. 1952, 51: 505 - 3b
Adams DR.Bhatnagar SR. Synthesis 1977, 661 - 3c
Snider BB. In Comprehensive Organic Synthesis Vol. 2:Trost BM. Pergamon; Oxford: 1991. p.527-561 - 4a
Coppi L.Ricci A.Taddi M. J. Org. Chem. 1988, 53: 911 - 4b
Brown MJ.Harrison T.Herrinton PM.Hopkins MH.Hutchinson KD.Mishra P.Overman LE. J. Am. Chem. Soc. 1991, 113: 5365 - 4c
Semeyn C.Blaauw RH.Hiemstra H.Speckamp WN. J. Org. Chem. 1997, 62: 3426 - 4d
Marko IE.Dobbs AP.Scheirmann V.Chelle F.Bayston DJ. Tetrahedron Lett. 1997, 38: 2899 - 4e
Rychnovsky SD.Hu Y.Ellsworth B. Tetrahedron Lett. 1998, 39: 7271 - 4f
Suginome M.Iwanami T.Ito Y. J. Org. Chem. 1998, 63: 6096 - 4g
Nishizaw M.Shigaraki T.Takao H.Imagawa H.Sugihara T. Tetrahedron Lett. 1999, 40: 1153 - 4h
Cloninger MJ.Overman LE. J. Am. Chem. Soc. 1999, 121: 1092 - 4i
Wei ZY.Li JS.Wang D.Chan TH. Tetrahedron Lett. 1987, 28: 3441 - 5a
Yang J.Li C.-J. Synlett 1999, 717 - 5b
Viswanathan GS.Yang J.Li C.-J. Org. Lett. 1999, 1: 993 - 5c
Zhang W.-C.Li C.-J. Tetrahedron 2000, 56: 2403 - 5d
Yang X.-F.Mague JT.Li C.-J. J. Org. Chem. 2001, 66: 739 - 5e
Keh CCK.Namboodiri VV.Varma RS.Li C.-J. Tetrahedron Lett. 2002, 43: 4993 - For leading references, see:
- 6a
Seddon KR. J. Chem. Technol. Biotechnol. 1997, 68: 351 - 6b
Welton T. Chem. Rev. 1999, 99: 2071 - 6c
Wasserscheid P.Keim W. Angew. Chem. Int. Ed. 2000, 39: 3772 - 6d
Sheldon R. Chem. Commun. 2001, 2399 - 7
Gewali MB.Tezuka Y.Banskota AH.Ali MS.Saiki I.Dong S.Kadota S. Org. Lett. 1999, 1: 1733 - 8a
Yang X.-F.Wang M.Varma RS.Li C.-J. Org. Lett. 2003, 5: 657 - 8b
Yang X.-F.Wang M.Li C.-J. J. Mol. Catal. A: Chem. 2004, 214: 147 - 9
Larock RC.Stolz-Dunn SK. Tetrahedron Lett. 1989, 30: 3487