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
Synthesis 2008(24): 3903-3918
DOI: 10.1055/s-0028-1083240
DOI: 10.1055/s-0028-1083240
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
A Concise Route to Difluorinated Analogues of Cyclitols and Sugars
Weitere Informationen
Received
5 September 2008
Publikationsdatum:
01. Dezember 2008 (online)
Publikationsverlauf
Publikationsdatum:
01. Dezember 2008 (online)
Abstract
Allyl ethers of trifluoroethanol are transformed to difluorinated analogues of deoxysugars via concise sequences involving dehydrofluorination/metallation, [3,3]-Claisen rearrangement, reduction, and RCM, affording cyclohexenediol substrates for dihydroxylation reactions.
Key words
carbasugars - cyclitols - difluorinated - metathesis - dihydroxylation
- 1
Schedler DJA.Baker DC. Carbohydr. Res. 2004, 339: 1585 -
2a
Pongdee R.Liu HW. Bioorg. Chem. 2004, 32: 393 -
2b
Yuan Y.Bleile DW.Wen X.Sanders DAR.Itoh K.Liu HW.Pinto BM. J. Am. Chem. Soc. 2008, 130: 3157 -
2c
Caravano A.Dohi H.Sinaÿ P.Vincent SP. Chem. Eur. J. 2006, 12: 3114 -
3a
Zhang R.McCarter JD.Braun C.Yeung W.Brayer GD.Withers SG. J. Org. Chem. 2008, 73: 3070 -
3b
Hart DO.He SM.Chany CJ.Withers SG.Sims PFG.Sinnott ML.Brumer H. Biochemistry 2000, 39: 9826 -
4a
Withers SG.McCarter JD.Howard S.Vocadlo D. Abstracts of Papers 214th National Meeting of the American Chemical Society; Las Vegas NV, Sept. 7-11, 1997: American Chemical Society: Washington, DC, 1997; CARB-4 -
4b
Namchuk MN.McCarter JD.Becalski A.Andrews T.Withers SG. J. Am. Chem. Soc. 2000, 122: 1270 -
4c
McCarter JD.Yeung W.Chow J.Dolphin D.Withers SG. J. Am. Chem. Soc. 1997, 119: 5792 -
5a
Sawyer DA.Potter BVL. Bioorg. Med. Chem. Lett. 1991, 1: 705 -
5b
Lampe D.Potter BVL. Tetrahedron Lett. 1993, 34: 2365 - 6
Eguchi T.Sasaki S.Huang Z.Kakinuma K. J. Org. Chem. 2002, 67: 3979 - 7 For a review, see:
Singh RP.Shreeve JM. Synthesis 2002, 2561 -
8a
Ellaghdach A.Echarri R.Matheu MI.Barrena MI.Castillon S.Garcia J. J. Org. Chem. 1991, 56: 4556 -
8b
Barrena MI.Matheu MI.Castillon S. J. Org. Chem. 1998, 63: 2184 -
8c
Aghmiz ML.Diaz Y.Jana GH.Matheu MI.Echarri R.Castillon S.Jimeno ML. Tetrahedron 2001, 57: 6733 - 9
Deleuze A.Menozzi C.Sollogoub M.Sinaÿ P. Angew. Chem. Int. Ed. 2004, 43: 6680 - 10 For a preliminary publication, see:
Audouard C.Fawcett J.Griffith GA.Kerouredan E.Miah A.Percy JM.Yang HL. Org. Lett. 2004, 6: 4269 - 11
Audouard C.Garayt MR.Kerouredan E.Percy JM.Yang HL. J. Fluorine Chem. 2005, 126: 611 -
12a
Metcalf BW.Jarvi ET.Burkhart JP. Tetrahedron Lett. 1985, 26: 2861 -
12b
DiMartino G.Percy JM. Chem. Commun. 2000, 2: 2339 - 13
Davis AP. In Houben-Weyl, Stereoselective Synthesis Vol. E21:Helmchen G.Hoffmann RW.Mulzer J. Georg Thieme Verlag; Stuttgart: 1996. p.3994 - 14 For a recent noviose synthesis,
see:
Hanessian S.Auzzas L. Org. Lett. 2008, 10: 261 - 15 For a review of deoxysugars and
their synthesis, see:
Kirschning A.Jesberger M.Schoning KU. Synthesis 2001, 507 - 16
Chatterjee AK.Choi TL.Sanders DP.Grubbs RH. J. Am. Chem. Soc. 2003, 125: 11360 - 17
Courchay FC.Baughman TW.Wagener KB. J. Organomet. Chem. 2006, 691: 585 - 18
Ulman M.Grubbs RH. Organometallics 1998, 17: 2484 - 19
Hong SH.Wenzel AG.Salguero TT.Day MW.Grubbs RH. J. Am. Chem. Soc. 2007, 129: 7961 - 20
VanRheenen V.Kelly RC.Cha DY. Tetrahedron Lett. 1976, 1973 -
21a
Donohoe TJ. Synlett 2002, 1223 -
21b
Donohoe TJ.Blades K.Moore PR.Waring MJ.Winter JJG.Helliwell M.Newcombe NJ.Stemp G. J. Org. Chem. 2002, 67: 7946 - 22
Cha JK.Christ WJ.Kishi Y. Tetrahedron 1984, 40: 2247 - 23
Cha JK.Kim NS. Chem. Rev. 1995, 95: 1761 - 24
Mulholland GK. Nuclear Med. Biol. 1995, 22: 19 -
25a
Iwasawa N.Kato T.Narasaka K. Chem. Lett. 1988, 1721 -
25b
Gypser A.Michel D.Nirschl DS.Sharpless KB. J. Org. Chem. 1998, 63: 7322 - 26
Duhamel L.Plaquevent JC. J. Organomet. Chem. 1993, 448: 1