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Synthesis 2007(5): 749-753
DOI: 10.1055/s-2007-965925
DOI: 10.1055/s-2007-965925
PAPER
© Georg Thieme Verlag Stuttgart · New York
Syntheses of 2-Pyrones via Electrophilic Substitutions at C7 of 4-Hydroxy-6-methyl-2-pyrone through Mono- or Dianion Formation
Further Information
Received
27 October 2006
Publication Date:
08 February 2007 (online)
Publication History
Publication Date:
08 February 2007 (online)
Abstract
Electrophilic substitution protocols useful for functionalizations at C7 of 4-hydroxy-6-methyl-2-pyrone, or triacetic acid, are described here. This method was applied to the synthesis of annularin E.
Key words
dianion - 2-pyrones - 4-hydroxy-6-methyl-2-pyrone - triacetic acid - electrophilic substitution
- 1 For a review, see:
Romines KR.Chrusciel RA. Curr. Med. Chem. 1995, 2: 825 - For recent reports, see:
-
2a
Fors KS.Gage JR.Heier RF.Kelly RC.Perrault WR.Wicnienski N. J. Org. Chem. 1998, 63: 7348 -
2b
Vara Prasad JVN.Tummino PJ.Ferguson D.Saunders J.Vander Roest S.McQuade TJ.Heldsinger A.Reyner EL.Stewart BH.Guttendorf RJ.Para KS.Lunney EA.Gracheck SJ.Domagala JM. Biochem. Biophys. Res. Commun. 1996, 221: 815 -
3a
Schwartz TM.Bundy GL.Strohbach JW.Thaisrivongs S.Johnson PD.Skulnick HI.Tomich PK.Lynn JC.Chong K.-T.Hinshaw RR.Raub TJ.Padbury GE.Toth LN. Bioorg. Med. Chem. Lett. 1997, 7: 399 -
3b
Thaisrivongs S.Janakiraman MN.Chong K.-T.Tomich PK.Dolak LA.Turner SR.Strohbach JW.Lynn JC.Horng M.-M.Hinshaw RR.Watenpaugh KD. J. Med. Chem. 1996, 39: 2400 -
3c
Thaisrivongs S.Watenpaugh KD.Howe WJ.Tomich PK.Dolak LA.Chong K.-T.Tomich CSC.Tomasselli AG.Turner SR.Strohbach JW.Mulichak AM.Janakiraman MN.Moon JB.Lynn JC.Horng M.-M.Hinshaw RR.Curry KA.Rothrock DJ. J. Med. Chem. 1995, 38: 3624 - 4 For isolation, see:
Shu Y.-Z.Ye Q.Li H.Kadow KF.Hussain RA.Huang S.Gustavson DR.Lowe SE.Chang LP.Pirnik DM.Kodukula K. Bioorg. Med. Chem. Lett. 1997, 7: 2295 - For recent synthetic efforts toward orevactaene, see:
-
5a
Organ MG.Bratovanov S. Tetrahedron Lett. 2000, 41: 6945 -
5b
Organ MG.Bilokin YV.Bratovanov S. J. Org. Chem. 2002, 67: 5176 - For isolation, see:
-
6a
Otoguro K.Kuno F.Õmura S. Pharmacol. Ther. 1997, 76: 45 -
6b
Otoguro K.Shiomi K.Yamaguchi Y.Arai N.Sunazuka T.Masuma R.Iwai Y.Õmura S. J. Antibiot. 2000, 53: 5 - 7 For a recent review on synthetic efforts toward arisugacin A, see:
Cole KP.Hsung RP. In Strategies and Tactics in Organic Synthesis Vol.4:Harmata M. Pergamon Press; Oxford: 2004. p.41-70 - For our total synthesis efforts, see:
-
8a
Hsung RP. J. Org. Chem. 1997, 62: 7904 -
8b
Zehnder LR.Hsung RP.Wang J.-S.Golding GM. Angew. Chem. Int. Ed. 2000, 39: 3876 -
8c
Cole KP.Hsung RP. Tetrahedron Lett. 2002, 43: 8791 -
8d
Cole KP.Hsung RP.Yang X.-F. Tetrahedron Lett. 2002, 43: 3341 -
8e
Hsung RP.Cole KP.Zehnder LR.Wang J.Wei LL.Yang X.-F.Coverdale HA. Tetrahedron 2003, 59: 311 - For isolation, see:
-
9a
Nair MSR.Carey ST. Tetrahedron Lett. 1975, 16: 3617 -
9b
Nair MSR. Phytochemistry 1976, 15: 1090 - 10
Shimizu T.Hiranuma S.Wantanabe T. Heterocycles 1993, 36: 2445 - 11 For a leading reference, see:
Katritzky AR.Wang Z.Wang M.Hall CD.Suzuki K. J. Org. Chem. 2005, 70: 4854 - For some examples, see:
-
12a
Organ MG.Wang J. J. Org. Chem. 2003, 68: 5568 -
12b
Hagiwara H.Kobayashi K.Hoshi T.Suzuki T.Ando M. Tetrahedron 2001, 57: 5039 -
12c
Lokot IP.Pashkovsky FS.Lakhvich FA. Tetrahedron 1999, 55: 4783 - 13
Douglas CJ.Sklenicka HM.Shen HC.Golding GM.Mathias DS.Degen SJ.Morgan CD.Shih RA.Mueller KL.Seurer LM.Johnson EW.Hsung RP. Tetrahedron 1999, 55: 13683 -
14a For an earlier report on generating the dianion from triacetic acid, see:
Wachter MP.Harris TM. Tetrahedron 1970, 26: 1685 - For C7 alkylations, see:
-
14b
Shimo T.Matsuzaki S.Somekawa K. J. Heterocycl. Chem. 1994, 31: 387 -
14c
Groutas WC.Stanga MA.Brubaker MJ.Huang TL.Moi MK.Carroll RT. J. Med. Chem. 1985, 28: 1106 -
14d
Poulton GA.Cyr TD. Can. J. Chem. 1982, 60: 2821 - For an addition to aldehyde, see:
-
14e
Oikawa H.Kobayashi T.Katayama K.Suzuki Y.Ichihara A. J. Org. Chem. 1998, 63: 8748 - For C7 oxidation, see:
-
14f
Suzuki E.Hamajima R.Inoue S. Synthesis 1975, 192 -
14g
Bacardit R.Moreno-Mañas M.Pleixats R. J. Heterocycl. Chem. 1982, 19: 157 - For bromination, see:
-
14h
Jones RCF.Patience JM. Tetrahedron Lett. 1989, 30: 3217 - 15 For an application of its utility, see:
McLaughlin MJ.Hsung RP.Cole KC.Hahn JM.Wang J. Org. Lett. 2002, 4: 2017 - 16
Li C.Nitka MV.Gloer JB. J. Nat. Prod. 2003, 66: 1302 - For some other recently isolated related 2-pyrone containing natural products, see:
-
17a
Cutignano A.Fontana A.Renzulli L.Cimino G. J. Nat. Prod. 2003, 66: 1399 -
17b
Pedras MSC.Chumala PB. Phytochemistry 2005, 66: 81 - 18 For an application of its utility, see:
Swidorski JJ.Wang J.Hsung RP. Org. Lett. 2006, 8: 777