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 2005(14): 2341-2344
DOI: 10.1055/s-2005-870025
DOI: 10.1055/s-2005-870025
PAPER
© Georg Thieme Verlag Stuttgart · New York
Convenient Synthesis of Volatile Streptomyces Lactones
Further Information
Received
20 January 2005
Publication Date:
14 July 2005 (online)
Publication History
Publication Date:
14 July 2005 (online)
Abstract
A convenient three-step synthetic approach towards 3-alkyl-5-methyl-2[5H]furanones is described. The steps involved in the synthesis are domino primary alcohol oxidation-Wittig reaction, acid-catalysed lactonisation and isomerisation. This synthetic approach has been exploited to synthesise four Streptomyces lactones.
Key words
domino reaction - Wittig reaction - isomerisation - lactone - oxidation
-
1a
Alali FQ.Liu X.-X.McLaughlin JL. J. Nat. Prod. 1999, 62: 504 -
1b
Mori K. Tetrahedron 1989, 45: 3233 -
1c
Dubs P.Stussi R. Helv. Chim. Acta 1978, 61: 990 -
1d
Gerber NN. Tetrahedron Lett. 1973, 771 -
2a
Hoye TR.Ye Z. J. Am. Chem. Soc. 1996, 118: 1801 -
2b
Mulzer J. Comprehensive Organic Functional Group Transformations Vol. 5:Katritzky AR.Meth-Cohn O.Rees CW. Elsevier; Oxford: 1995. p.121-180 -
2c
Hoppe R.Scharf H.-D. Synthesis 1995, 1447 -
2d
Yao Z.-J.Wu Y.-L. J. Org. Chem. 1995, 60: 993 -
2e
Black HT.Brown GA.Smith DC.Martinie SM. Synth. Commun. 1995, 25: 479 -
2f
Yao Z.-J.Wu Y.-L. Tetrahedron Lett. 1994, 35: 157 -
2g
Burke SD.Pacofsky GJ.Piscopio AD. J. Org. Chem. 1992, 57: 2228 -
2h
Jacobi PA.Touchette KM.Selnik HG. J. Org. Chem. 1992, 57: 6305 -
2i
Hoye TR.Hanson PR.Kovelesky AC.Ocain TD.Zhuang Z. J. Am. Chem. Soc. 1991, 113: 9369 -
2j
Zhang K.-Y.Borgerding AJ.Carlson RM. Tetrahedron Lett. 1988, 29: 5703 -
2k
Martin SF.Moore DR. Tetrahedron Lett. 1976, 4459 - 3
Dijstra FY.Wiken TO. Z. Lebensm. Unters. Forsch. 1973, 160: 263 - 4
Mikayado M.Kato T.Ohno N.Yoshioka H.Ohshio H. Agric. Biol. Chem. 1977, 41: 57 - 5
Corbera J.Font M.Monsalvatje RM.Ortuno F.Sanchez-Ferrando F. J. Org. Chem. 1988, 53: 4393 - 6
Ratnayake R.Karunaratne V.Ratnayake Bandara BM.Kumar V.MacLeod JK.Simmonds P. J. Nat. Prod. 2001, 64: 376 - 7
Tietze LF. Chem. Rev. 1996, 96: 195 - 8
Shet JB.Desai VG.Tilve SG. Synthesis 2004, 1859 -
9a
Nishide K.Aramat A.Kamanaka T.Inoue T.Node M. Tetrahedron 1994, 50: 8337 -
9b
Nishide K.Aramat A.Kamanaka T.Node M. Heterocycles 1993, 36: 2237 - 10
Matsui S. Bull. Chem. Soc. Jpn. 1987, 60: 1853 - 11
Crich D.Mo X.-S. Synlett 1999, 67 - 12
Mali RS.Tilve SG.Yeola SN.Manekar AR. Heterocycles 1987, 26: 121