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 2002(1): 0111-0115
DOI: 10.1055/s-2002-19302
DOI: 10.1055/s-2002-19302
PAPER
© Georg Thieme Verlag Stuttgart · New YorkA Convenient Route to Alkaloid Lipids: Application for the Synthesis of a Leptophylline A Analogue
Weitere Informationen
Received
31 July 2001
Publikationsdatum:
04. August 2004 (online)
Publikationsverlauf
Publikationsdatum:
04. August 2004 (online)
Abstract
A synthetic route for efficient access to alkaloid lipids, using the chiral 2,3,6-trisubstituted piperidine acetaldehyde 9 as an intermediate, is reported. The utility of the synthetic route was demonstrated in the asymmetric synthesis of an unnatural analogue of Cassia leptophylla alkaloid lipid, leptophyllin A, in 16 steps and 15% overall yield starting from d-glucal.
Key words
piperidines - alkaloids - asymmetric synthesis
- 1
Schneider MJ. In Alkaloids: Chemical and Biological Perspectives Vol. 10:Pelletier SW. Pergamon Press; Oxford: 1996. p.155-299 - 2a
Astudillo SL.Jürgens SK.Schmeda-Hirschman G.Griffith GA.Holt DH.Jenkins PR. Planta Med. I 1999, 65: 161 - 2b
Jones TH.Blum MS.Robertson HG. J. Nat. Prod. 1990, 53: 429 - 2c
Roth HJ.Kleemann A. In Pharmaceutical Chemistry John Wiley & Sons; New York: 1988. - 2d
Strunz GM.Findlay JA. In Alkaloids Vol 26:Brossi A. Academic Press; New York: 1985. p.89-183 - 3 For a comprehensive recent review on stereoselective synthesis of Prosopis and Cassia piperidine alkaloids see:
Laschat S.Dickner T. Synthesis 2000, 1781 - Some representative recent articles:
- 4a
Datta A.Kumar JSR.Roy S. Tetrahedron 2001, 57: 1169 - 4b
Enders D.Kirchhoff JH. Synthesis 2000, 2099 - 4c
Herdeis C.Telser J. Eur. J. Org. Chem. 1999, 1407 - 4d
Herdeis C.Schiffer T. Tetrahedron 1999, 55: 1043 - 4e
Ojima I.Vidal ES. J. Org. Chem. 1998, 63: 7999 - 5
Bolzani VS.Gunatilaka AAL.Kingston DGI. Tetrahedron 1995, 51: 5929 - 6a
Koulocheri SD.Haroutounian SA. Tetrahedron Lett. 1999, 40: 6869 - 6b
Koulocheri SD.Magiatis P.Skaltsounis A.-L.Haroutounian SA. Tetrahedron 2000, 56: 6135 - 7
Koulocheri SD.Haroutounian SA. Synthesis 1999, 1889 - 8 For a recent review on this subject see:
Speckamp WN.Moolenaar MJ. Tetrahedron 2000, 56: 3817 - 9a
Cook GR.Beholz LG.Stille JR. J. Org. Chem. 1994, 59: 3575 - 9b
Cook GR.Beholz LG.Stille JR. Tetrahedron Lett. 1994, 35: 1669