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 2011(6): 901-904
DOI: 10.1055/s-0030-1258431
DOI: 10.1055/s-0030-1258431
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Stereoselective Synthesis of (-)-Galantinic Acid
Weitere Informationen
Received
28 December 2010
Publikationsdatum:
10. Februar 2011 (online)
Publikationsverlauf
Publikationsdatum:
10. Februar 2011 (online)

Abstract
An efficient and highly concise synthesis of (-)-galantinic acid has been achieved using an asymmetric allylation reaction of Garner’s aldehyde.
Key words
chiral pool - amino alcohol - iterative asymmetric allylation - oxidation - stereoselective synthesis
- 1
Shoji J.Sakajaki R.Koizumi K.Matsurra SJ. J. Antibiot. 1975, 28: 122 -
2a
Sakai N.Ohfune Y. Tetrahedron Lett. 1990, 31: 4151 -
2b
Sakai N.Ohfune Y. J. Am. Chem. Soc. 1992, 114: 998 -
3a
Ikota N. Heterocycles 1991, 32: 521 -
3b
Kumar JSR.Datta A. Tetrahedron Lett. 1999, 40: 1381 -
3c
Kiyooka S.Goh K.Nakamura Y.Takesue H.Hena MA. Tetrahedron Lett. 2000, 41: 6599 -
3d
Moreau X.Campagne J. Tetrahedron Lett. 2001, 42: 4467 -
3e
Bethuel Y.Gademann K. Synlett 2006, 1580 -
3f
Nagaiah K.Sreenu D.Purnima KV.Rao RS.Yadav JS. Synthesis 2009, 1386 -
3g
Dhorate B.Chattopadhyay A. Tetrahedron: Asymmetry 2009, 20: 2007 -
3h
Raghavan S.Ramakrishna Reddy S. J. Org. Chem. 2003, 68: 5754 -
3i
Pandey SK.Kandula SR.Kumar P. Tetrahedron Lett. 2004, 45: 5877 -
3j
Dubey A.Kauloorkar SH.Kumar P. Tetrahedron 2010, 66: 3159 -
4a
Jha V.Kondekar NB.Kumar P. Org. Lett. 2010, 12: 2762 -
4b
Kumar P.Gupta P.Naidu SV. Chem. Eur. J. 2006, 12: 1397 -
5a
Kumar P.Naidu SV.Gupta P. J. Org. Chem. 2005, 70: 2843 -
5b
Kumar P.Naidu SV. J. Org. Chem. 2005, 70: 4207 -
5c
Kumar P.Gupta P.Naidu SV. Chem. Eur. J. 2006, 12: 1397 -
5d
Kumar P.Naidu SV. J. Org. Chem. 2006, 71: 3935 -
5e
Gupta P.Kumar P. Eur. J. Org. Chem. 2008, 1195 -
5f
Kumar P.Pandey M.Gupta P.Naidu SV.Dhavale DD. Eur. J. Org. Chem. 2010, 6993 -
6a
Fernandes RA.Kumar P. Eur. J. Org. Chem. 2000, 3447 -
6b
Kumar P.Bodas MS. J. Org. Chem. 2005, 70: 360 -
6c
Dubey A.Kumar P. Tetrahedron Lett. 2009, 50: 3425 -
6d
Dubey A.Puranik VG.Kumar P. Org. Biomol. Chem. 2010, 8: 5074 ; and references cited therein - 7
Hafner A.Duthaler RO.Marti R.Rihs G.Rothe-Streit P.Schwarzenbach F. J. Am. Chem. Soc. 1992, 114: 2321 -
8a
Pappo R.Alen DS.Lemieux RU.Johnson WS. J. Org. Chem. 1956, 21: 478 -
8b
Wensheng Y.Yan M.Ying K.Zhengmao H.Zhendong J. Org. Lett. 2004, 6: 3217 -
9a
Duthaler RO.Hafner A. Chem. Rev. 1992, 92: 807 -
9b
Cossy J.BouzBouz S.Pradaux F.Willis C.Bellosta V. Synlett 2002, 1595 -
9c
BouzBouz S.Cossy J. Org. Lett. 2000, 2: 501 -
9d
BouzBouz S.Cossy J. Org. Lett. 2004, 6: 3469 -
9e
Allais F.Cossy J. Org. Lett. 2006, 8: 3655 -
9f
Amans D.Bellosta V.Cossy J. Org. Lett. 2007, 9: 1453 -
9g
Hassan A.Lu Y.Krische MJ. Org. Lett. 2009, 11: 3112 -
9h
Menz H.Kirsch SF. Org. Lett. 2009, 11: 5634 -
9i
Zhang ZY.Aubry S.Kishi Y. Org. Lett. 2008, 10: 3077 -
9j
Umarye JD.Lebmann T.Garcia AB.Mamane V.Sommer S.Waldmann H. Chem. Eur. J. 2007, 13: 3305 - 10
Shi Y.Peng LF.Kishi Y. J. Org. Chem. 1997, 62: 5666