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Synthesis 2010(14): 2446-2450
DOI: 10.1055/s-0029-1218774
DOI: 10.1055/s-0029-1218774
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
A Concise, Enantioselective Synthesis of (+)-Decarestrictine L from Tri-O-acetyl-d-glucal
Further Information
Received
8 March 2010
Publication Date:
05 May 2010 (online)
Publication History
Publication Date:
05 May 2010 (online)
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Abstract
We describe a new and efficient approach to the enantioselective synthesis of (+)-(2R,3S,6R)-decarestrictine L from commercially available tri-O-acetyl-d-glucal, based on a stereoselective Michael addition.
Key words
Michael addition - Wolf-Kishner reaction - Wacker oxidation
- 1
Grabley S.Hammann P.Huetter K.Kirsch R.Kluge H.Thiericke R.Mayer M.Zeeck A. J. Antibiot. 1992, 45: 1176 -
2a
Göhrt A.Zeeck A.Hüetter K.Kirsch R.Kluge H.Thiericke R. J. Antibiot. 1992, 45: 66 -
2b
Mayer M.Thiericke R. J. Antibiot. 1993, 46: 1372 -
3a
Machinaga N.Kibayashi C. Tetrahedron Lett. 1993, 34: 5739 -
3b
Clark JS.Whitlock GA. Tetrahedron Lett. 1994, 35: 6381 -
3c
Nokami J.Taniguchi T.Ogawa Y. Chem. Lett. 1995, 43 -
3d
Solladié G.Arce E.Bauder C.Carreño MC. J. Org. Chem. 1998, 63: 2332 -
3e
Esumi T.Kimura R.Mori M.Iwabuchi Y.Irie H.Hatakeyama S. Heterocycles 2000, 52: 525 -
3f
Lukesh JM.Donaldson WA. Tetrahedron: Asymmetry 2003, 14: 757 -
3g
García I.Gómez G.Teijeira M.Terán C.Fall Y. Tetrahedron Lett. 2006, 47: 1333 -
3h
Clark JS.Fessard TC.Whitlock GA. Tetrahedron 2006, 62: 73 - 4 For a recent review on biological
and synthetic studies on the decarestrictine family during the last
fifteen years, see:
Riatto VB.Pilli RA.Victor MM. Tetrahedron 2008, 64: 2279 - 6
Mori Y.Hayashi H. J. Org. Chem. 2001, 66: 8666 -
7a
Hutchins RO.Milewski CA.Maryanoff BE. J. Am. Chem. Soc. 1973, 95: 3662 -
7b
Davies MJ.Moody CJ. J. Chem. Soc., Perkin Trans. 1 1991, 1: 9 - 8
Marshall JA.Crooks SL.DeHoff BS. J. Org. Chem. 1988, 53: 1616 -
9a
Tsuji J.Shiizu I.Yamamoto K. Tetrahedron Lett. 1976, 34: 2975 -
9b
Clark JS.Fessard TC.Whitlock GA. Tetrahedron 2006, 62: 73 - 10 For our preliminary results of QSAR
studies on decarestrictine L, see:
García I.Munteanu CR.Fall Y.Gómez G.Uriarte E.Gonzalez-Diaz H. Bioorg. Med. Chem. 2009, 17: 165
References
Although d-glucal is commercially available, tri-O-acetyl-d-glucal is much cheaper and can be used for large-scale synthesis.