Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2006(1): 63-72
DOI: 10.1055/s-2005-918441
DOI: 10.1055/s-2005-918441
PAPER
© Georg Thieme Verlag Stuttgart · New York
Convenient Synthesis of Substituted α-Methylene-δ-valerolactones in Aqueous Medium Using Baylis-Hillman Chemistry [1]
Further Information
Received
15 June 2005
Publication Date:
27 October 2005 (online)
Publication History
Publication Date:
27 October 2005 (online)
Abstract
A mild and convenient synthesis of substituted α-methylene-δ-valerolactones was achieved by SN2 nucleophilic substitution of the acetates of Baylis-Hillman adducts with acetyl acetone followed by one-pot saponification of the ester, reduction of the keto group, and subsequent intramolecular ring closure in aqueous medium.
Key words
Baylis-Hillman - α-methylene-δ-valerolactone - nucleophilic substitution - aqueous medium
CDRI Communication No. 6732.
- 2
Kupchan SM.Hemingway RJ.Werner D.Karim A.McPhail AT.Sim GA. J. Am. Chem. Soc. 1968, 90: 3596 -
3a
Liao X.-B.Han J.-Y.Li Y. Tetrahedron Lett. 2001, 42: 2843 -
3b
Ekthawatchai S.Kamchonwongpaisan S.Kongsaeree P.Tarnchompoo B.Thebtaranonth Y.Yuthavong Y. J. Med. Chem. 2001, 44: 4688 -
3c
Avery MA.Alvim-Gaston M.Vroman JA.Wu B.Ager A.Peters W.Robinson BL.Charman W. J. Med. Chem. 2002, 45: 4321 - 4
Cane DE.Rossi T. Tetrahedron Lett. 1979, 20: 2973 - 5
Nangia A.Prasuna G.Rao PB. Tetrahedron 1997, 53: 14507 -
6a
Weinheimer AJ.Chang CWJ.Matson JA. Fortschr. Chem. Org. Naturst. 1979, 36: 2385 -
6b
McMurry JE.Dushin RG. J. Am. Chem. Soc. 1990, 112: 5967 -
7a
Demuth M.Schaffner K. Angew. Chem., Int. Ed. Engl. 1982, 21: 820 -
7b
Giese B.Hoch M.Lamberth C.Schmidt RR. Tetrahedron Lett. 1988, 29: 1375 -
7c
Takeda K.Imaoka I.Yoshii E. Tetrahedron 1994, 50: 10839 -
7d
Soiladié G.Boeffel D.Maignan J. Tetrahedron 1995, 51: 9559 -
7e
Soiladié G.Boeffel D.Maignan J. Tetrahedron 1996, 52: 2065 -
8a
Grieco PA. Synthesis 1975, 67 -
8b
Ksander GM.McMurry JE.Johnson M. J. Org. Chem. 1977, 42: 1180 -
8c
Ghera E.Yechezkel T.Hassner A. J. Org. Chem. 1990, 55: 5977 -
8d
Paterson I.Fleming I. Tetrahedron Lett. 1979, 993 -
8e
Ochiai M.Fujita E.Arimoto M.Yamaguchi H. Tetrahedron Lett. 1983, 24: 777 -
8f
Carlson MR.White LL. Synth. Commun. 1983, 13: 237 -
8g
Mori M.Washioka Y.Urayama T.Yoshiura K.Chiba K.Ban Y. J. Org. Chem. 1983, 48: 4058 -
8h
Lee E.Hur CU.Park CM. Tetrahedron Lett. 1990, 35: 5039 -
8i
Nishitani K.Harada Y.Nakamura Y.Yokoo K.Yamakawa K. Tetrahedron Lett. 1994, 35: 7809 -
8j
Gupta A.Vankar YD. Tetrahedron 2000, 56: 8525 -
8k
Krawczyk H.Sliwinski M. Tetrahedron 2003, 59: 9199 -
8l
Krawczyk H.Sliwinski M.Wolf WM.Bodalski R. Synlett 2004, 1995 - 9
Noyori R. Chem. Commun. 2005, 1807 - 10
Masuyama Y.Nimura Y.Kurusu Y. Tetrahedron Lett. 1991, 32: 225 - 11
Adam W.Salagado VON.Peters E.-M.Peters K.von Schnering HG. Chem. Ber. 1993, 126: 1481 - 12
Martinez I.Andrews AE.Emch JD.Ndakala AJ.Wang J.Howell AR. Org. Lett. 2003, 5: 399 - 13
Brezinski LJ.Rafel S.Leahy JW. J. Am. Chem. Soc. 1997, 119: 4317 -
14a
Bauchat P.Le Rouille E.Foucad A. Bull. Soc. Chim. Fr. 1991, 267 -
14b
Chamakh A.Amri H. Tetrahedron Lett. 1998, 39: 375 - 15
Choudhury PK.Foubelo F.Yus M. Tetrahedron Lett. 1998, 39: 3581 - 16
Paquette LA.Mendez-Adino J. Tetrahedron Lett. 1999, 40: 4301 - 17
Schneider MF.Blechert S.Matuszak A.Pickardt J. Synlett 1999, 638 - 18
Gonzalez AG.Silva MH.Padron JI.Leon F.Reyes E.Alvarez-Mon M.Pivel JP.Quintana J.Estevez F.Bermejo J. J. Med. Chem. 2002, 45: 2358 -
19a
Patra A.Batra S.Kundu B.Joshi BS.Roy R.Bhaduri AP. Synthesis 2001, 276 -
19b
Cai J.Zhou Z.Zhao G.Tang C. Org. Lett. 2002, 4: 4723 -
19c
Roy AK.Batra S. Synthesis 2003, 1347 -
19d
Roy AK.Batra S. Synthesis 2003, 2325
References
CDRI Communication No. 6732.