RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
PDF herunterladen
Synthesis 2010(3): 505-509
DOI: 10.1055/s-0029-1218588
DOI: 10.1055/s-0029-1218588
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New YorkSynthesis of the C1-C13 Subunit of Spirastrellolides A and B by Prins Cyclization
Weitere Informationen
Received
26 August 2009
Publikationsdatum:
07. Dezember 2009 (online)
Publikationsverlauf
Publikationsdatum:
07. Dezember 2009 (online)
Abstract
The C1-C13 subunit of the marine natural products spirastrellolides A and B, which contains a cis-substituted tetrahydropyran ring, was prepared by using the Prins cyclization strategy.
Key words
tetrahydropyrans - diastereoselectivity - homoallylic alcohols - aldehydes - cyclizations
- 1a
Blunt JW.Copp BR.Munro MHG.Northcote PT.Prinsep MR. Nat. Prod. Rep. 2005, 22: 15 - 1b
Newman DJ.Cragg GM. J. Nat. Prod. 2004, 67: 1216 - 1c
Yeung K.-S.Paterson I. Chem. Rev. 2005, 105: 4237 - 2a
Williams DE.Roberge M.Van Soest R.Andersen RJ. J. Am. Chem. Soc. 2003, 125: 5296 - 2b
Williams DE.Roberge M.Andersen RJ. Org. Lett. 2004, 6: 2607 - 3
Williams DE.Keyzers RA.Warabi K.Desjardine K.Jenna L.Riffell JL.Roberge M.Andersen RJ. J. Org. Chem. 2007, 72: 9842 - 4
Warabi K.Williams DE.Patrick BO.Roberge M.Andersen RJ. J. Am. Chem. Soc. 2007, 129: 508 - 5a
Liu J.Hsung RP. Org. Lett. 2005, 7: 2273 - 5b
Paterson I.Anderson EA.Dalby SM.Loiseleur O. Org. Lett. 2005, 7: 4125 - 5c
Paterson I.Anderson EA.Dalby SM.Loiseleur O. Org. Lett. 2005, 7: 4121 - 5d
Liu J.Yang JH.Ko C.Hsung RP. Tetrahedron Lett. 2006, 47: 6121 - 5e
Ghosh SK.Ko C.Liu J.Wang J.Hsung RP. Tetrahedron 2006, 62: 10485 - 5f
Fürstner A.Fenster MDB.Fasching B.Godbout C.Radkowski K. Angew. Chem. Int. Ed. 2006, 45: 5510 - 5g
Yang JH.Liu J.Hsung RP. Org. Lett. 2008, 10: 2525 - 5h
Paterson I.Anderson EA.Dalby SM.Lim JH.Maltas P.Moessner C. Chem. Commun. 2006, 4186 - 5i
Pan Y.De Brabander JK. Synlett 2006, 853 - 5j
Wang C.Forsyth CJ. Org. Lett. 2006, 8: 2997 - 5k
Paterson I.Anderson EA.Dalby SM.Genovino J.Lim JH.Moessner C. Chem. Commun. 2007, 1852 - 5l
Fürstner A.Fenster MDB.Fasching B.Godbout C.Radkowski K. Angew. Chem. Int. Ed. 2006, 45: 5506 - 5m
Fürstner A.Fasching B.O’Neil GW.Fenster MDB.Godbout C.Ceccon J. Chem. Commun. 2007, 3045 - 5n
Wang C.Forsyth CJ. Heterocycles 2007, 72: 621 - 5o
Smith AB.Kim D.-S. Org. Lett. 2007, 9: 3311 - 5p
Keaton KA.Phillips AJ. Org. Lett. 2008, 10: 1083 - 5q
Chandrasekhar S.Rambabu C.Reddy AS. Org. Lett. 2008, 10: 4355 - 5r
Paterson I.Anderson EA.Dalby SM.Lim JH.Genovino J.Maltas P.Moessner C. Angew. Chem. Int. Ed. 2008, 47: 3016 - 5s
Paterson I.Anderson EA.Dalby SM.Lim JH.Genovino J.Maltas P.Moessner C. Angew. Chem. Int. Ed. 2008, 47: 3021 - 6a
Newmann DJ.Cragg GM. J. Nat. Prod. 2007, 70: 461 - 6b
Koehn FE.Carter GT. Nat. Rev. Drug Discovery 2005, 4: 206 - 6c
Bialy L.Waldmann H. Angew. Chem. Int. Ed. 2005, 44: 3814 - 6d
McCluskey A.Sim ATR.Sakoff JA. J. Med. Chem. 2002, 45: 1151 - 6e
Honkanen RE.Golden T. Curr. Med. Chem. 2002, 9: 2055 - 7a
Rychnovsky SD.Thomas CR. Org. Lett. 2000, 2: 1217 - 7b
Yang X.-F.Mague JT.Li C.-J. J. Org. Chem. 2001, 66: 739 - 7c
Barry CStJ.Crosby SR.Harding JR.Hughes RA.King CD.Parker GD.Willis CL. Org. Lett. 2003, 5: 2429 - 7d
Crosby SR.Harding JR.King CD.Parker GD.Willis CL. Org. Lett. 2002, 4: 3407 - 7e
Rychnovsky SD.Hu Y.Ellsworth B. Tetrahedron Lett. 1998, 39: 7271 - 7f
Semeyn C.Blaauw RH.Hiemstra H.Speckamp WN. J. Org. Chem. 1997, 62: 3426 - 7g
Cloninger MJ.Overman LE. J. Am. Chem. Soc. 1999, 121: 1092 - 7h
Suginome M.Iwanami T.Ito Y. J. Org. Chem. 1998, 63: 6096 - 8
Sabitha G.Bhikshapathi M.Yadav JS. Tetrahedron Lett. 2006, 47: 2807 - 9a
Sabitha G.Reddy KB.Reddy GSKK.Narjis F.Yadav JS. Synlett 2005, 2347 - 9b
Sabitha G.Narjis F.Reddy EV.Yadav JS. Tetrahedron Lett. 2008, 49: 6087 - 9c
Sabitha G.Narjis F.Gopal P.Reddy CN.Yadav JS. Tetrahedron: Asymmetry 2009, 20: 184 - 10
Schaus SE.Brandes BD.Larrow JF.Tokunaga M.Hansen KB.Gould AE.Furrow ME.Jacobsen E. J. Am. Chem. Soc. 2002, 124: 1307 - 11
Hansen TV. Tetrahedron: Asymmetry 2002, 13: 547 - 12
Sabitha G.Bhaskar V.Yadav JS. Tetrahedron Lett. 2006, 47: 8179 - 13
Holmquist CR.Roskamp EJ. J. Org. Chem. 1989, 54: 3258 - 14a
Evans DA.Hoveyda AH. J. Am. Chem. 1990, 112: 6447 - 14b
Schneider C.Klapa K.Hansch M. Synlett 2005, 91 - 14c
La Cruz TE.Rychnovsky SD. J. Org. Chem. 2007, 72: 2602 - 15
Rychnovsky SD.Rogers B.Yang G. J. Org. Chem. 1993, 58: 3511