Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2011(6): 979-983
DOI: 10.1055/s-0030-1259487
DOI: 10.1055/s-0030-1259487
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
First and Efficient Synthesis of 14-Aminophenanthroindolizidine Alkaloids
Further Information
Received
29 November 2010
Publication Date:
24 February 2011 (online)
Publication History
Publication Date:
24 February 2011 (online)

Abstract
14-Aminophenanthroindolizidine alkaloids and their N-acyl derivatives were prepared by a concise and efficient route involving a Parham-type cyclization as the key step.
Key words
alkaloids - metalations - cyclizations - drugs
- Supporting Information for this article is available online:
- Supporting Information
- 1
Gellert E. In The Alkaloids: Chemical and Biological Perspectives Vol. 5:Pelletier SW. Academic Press; New York: 1987. p.55-132 - 2
Suffness M.Cordell GA. In The Alkaloids: Chemistry and Pharmacology Vol. 25:Brossi A. Academic Press; Orlando: 1985. p.3-355 - 4
Gao W.Lam W.Zhong S.Kaczmarek C.Baker DC.Cheng YC. Cancer Res. 2004, 64: 678 -
5a
An T.-Y.Huang R.-Q.Yang Z.Zhang D.-K.Li G.-R.Yao Y.-C.Gao J. Phytochemistry 2001, 58: 1267 -
5b
Wang QM,Wang KL,Huang ZQ,Liu YX,Li H,Hu TS,Jin Z,Fan ZJ, andHuang RQ. inventors; CN 101189968. ; Chem. Abstr. 2008, 149, 97630 - For the most recent examples, see:
-
6a
Kim S.Lee J.Lee T.Park HG.Kim D. Org. Lett. 2003, 5: 2703 -
6b
Kim S.Lee T.Lee E.Lee J.Fan GJ.Lee SK.Kim D. J. Org. Chem. 2004, 69: 3144 -
6c
Furstner A.Kennedy JW. Chem. Eur. J. 2006, 12: 7398 -
6d
Kim S.Lee YM.Lee J.Lee T.Fu Y.Song Y.Cho J.Kim D. J. Org. Chem. 2007, 72: 4886 -
6e
Zeng W.Chemler SR. J. Org. Chem. 2008, 73: 6045 -
6f
McIver A.Young DD.Deiters A. Chem. Commun. 2008, 39: 4750 -
6g
Yamashita S.Kurono N.Senboku H.Tokuda M.Orito K. Eur. J. Org. Chem. 2009, 1173 -
6h
Rossiter LM.Slater ML.Giessert RE.Sakwa SA.Herr RJ. J. Org. Chem. 2009, 74: 9554 -
6i
Stoye A.Opatz T. Org. Lett. 2010, 12: 214 -
6j
Yang XM.Shi Q.Bastow KF.Lee KH. Org. Lett. 2010, 12: 1416 -
6k
Ambrosini LM.Cernak TA.Lambert TH. Tetrahedron 2010, 66: 4882 - 7
Wang ZW.Li Z.Wang KL.Wang QM. Eur. J. Org. Chem. 2010, 292 - 8
Wang ZW.Wang QM. Tetrahedron Lett. 2010, 51: 1377 -
9a
Bradsher CK.Hunt DA. J. Org. Chem. 1981, 46: 327 -
9b
Parham WE.Bradsher CK. Acc. Chem. Res. 1982, 15: 300 -
9c
Collado MI.Lete E.Sotomayor N.Villa MJ. Tetrahedron Lett. 1995, 51: 4701 -
9d
Collado MI.Sotomayor N.Villa MJ.Lete E. Tetrahedron Lett. 1996, 37: 6193 -
9e
Collado MI.Manteca I.Sotomayor N.Villa MJ.Lete E. J. Org. Chem. 1997, 62: 2080 -
9f
Ardeo A.Lete E.Sotomayor N. Tetrahedron Lett. 2000, 41: 5211 -
9g
Ruiz J.Sotomayor N.Lete E. Org. Lett. 2003, 5: 1115 -
9h
Moreau A.Couture A.Deniau E.Grandclaudon P. Eur. J. Org. Chem. 2005, 3437 -
9i
Ruiz J.Ardeo A.Ignacio R.Sotomayor N.Lete E. Tetrahedron 2005, 61: 3311 -
9j
Ruiz J.Lete E.Sotomayor N. Tetrahedron 2006, 62: 6182 -
9k
Lamblin M.Couture A.Deniau E.Grandclaudon P. Tetrahedron 2007, 63: 2664
References
The 60-cell line NCI test data, along with in vivo data, can be accessed from the corresponding NSC numbers at the following Web site: http://dtp.nci.nih.gov/dtpstandard/dwindex/index.jsp