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Synthesis 2007(24): 3807-3814
DOI: 10.1055/s-2007-990883
DOI: 10.1055/s-2007-990883
PAPER
© Georg Thieme Verlag Stuttgart · New York
Synthetic Studies towards the Total Synthesis of Providencin
Further Information
Received
17 July 2007
Publication Date:
13 November 2007 (online)
Publication History
Publication Date:
13 November 2007 (online)

Abstract
A synthetic approach to assemble the uncommon furylcyclobutane substructure in providencin has been developed starting from a commercially available cyclobutane precursor.
Key words
furans - cyclizations - natural products - stereoselective synthesis - total synthesis
- For recent reviews, see:
-
1a
Keay BA.Dibble PW. In Comprehensive Heterocyclic Chemistry II Vol. 2:Katritzky AR.Rees CW.Scriven EFV. Elsevier; Oxford: 1997. p.395 -
1b
Hou X.-L.Yang Z.Wong HNC. In Progress in Heterocyclic Chemistry Vol. 15:Gribble GW.Joule JA. Pergamon; Oxford: 2003. p.167 -
1c
Hou X.-L.Yang Z.Yeung K.-S.Wong HNC. In Progress in Heterocyclic Chemistry Vol. 17:Gribble GW.Joule JA. Pergamon; Oxford: 2005. p.142 - For recent reviews, see:
-
2a
Lipshutz BH. Chem. Rev. 1986, 86: 795 -
2b
Cacchi S. J. Organomet. Chem. 1999, 576: 42 -
2c
Keay BA. Chem. Soc. Rev. 1999, 28: 209 -
2d
Wong HNC.Yu P.Yick C.-Y. Pure Appl. Chem. 1999, 71: 1041 -
2e
Brown RCD. Angew. Chem. Int. Ed. 2005, 44: 850 ; Angew. Chem. 2005, 117, 872 -
2f
Lee H.-K.Chan K.-F.Hui C.-W.Yim H.-K.Wu X.-W.Wong HNC. Pure Appl. Chem. 2005, 77: 139 -
2g
Wright DL. In Progress in Heterocyclic Chemistry Vol. 17:Gribble GW.Joule JA. Pergamon; Oxford: 2005. p.1 -
2h
Kirsch SF. Org. Biomol. Chem. 2006, 4: 2076 - For recent furan syntheses, see, for example:
-
2i
Pridmore SJ.Slatford PA.Williams JM. Tetrahedron Lett. 2007, 48: 5111 -
2j
Peng L.Zhang X.Ma W.Wang J. Angew. Chem. Int. Ed. 2007, 46: 1905 ; Angew. Chem. 2007, 119, 1937 -
3a
Fenical W.Okuda RK.Bandurraga MM.Culver P.Jacobs RS. Science 1981, 212: 1512 -
3b
Fenical W. J. Nat. Prod. 1987, 50: 1001 -
3c
Wright AE.Burres NS.Schulte GK. Tetrahedron Lett. 1989, 30: 3491 -
3d
Abramson SN.Trischman JA.Tapiolas DM.Harold EE.Fenical W.Taylor P. J. Med. Chem. 1991, 34: 1798 -
3e
Gutiérrez M.Capson TL.Guzmán HM.González J.Ortega-Barría E.Quiñoá E.Riguera R. J. Nat. Prod. 2005, 68: 614 -
4a
Paquette LA.Doherty AM.Rayner CM. J. Am. Chem. Soc. 1992, 114: 3910 -
4b
Marshall JA.Van Devender EA. J. Org. Chem. 2001, 66: 8037 -
4c
Wipf P.Soth MJ. Org. Lett. 2002, 4: 1787 -
4d
Cases M.Gonzalez-Lopez de Turiso F.Hadjisoteriou MS.Pattenden G. Org. Biomol. Chem. 2005, 3: 2786 - 5 This expression is coined after the ‘furan last’ approach described by:
Marshall JA.DuBay WJ. J. Org. Chem. 1994, 59: 1703 - 6
Marrero J.Rodríguez AD.Baran P.Raptis RG. Org. Lett. 2003, 5: 2551 - 7
Bray CD.Pattenden G. Tetrahedron Lett. 2006, 47: 3937 - 8
Holmquist CR.Roskamp EJ. J. Org. Chem. 1989, 54: 3258 - 9
Ahmed A.Hoegenauer EK.Enev VS.Hanbauer M.Kaehlig H.Öhler E.Mulzer J. J. Org. Chem. 2003, 68: 3026