First and Efficient Synthesis
of 14-Aminophenanthroindolizidine Alkaloids

Ziwen Wang; Lei Wang; Qingmin Wang

doi:10.1055/s-0030-1259487

PAPER

First and Efficient Synthesis of 14-Aminophenanthroindolizidine Alkaloids

Ziwen Wang, Lei Wang, Qingmin Wang*
State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P. R. of China
Fax: 0086-022-23499842; e-Mail: wangqm@nankai.edu.cn;

Abstract

All articles of this category

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

Full Text

References

<A NAME="RF21310SS-1">1</A> Gellert E. In The Alkaloids: Chemical and Biological Perspectives Vol. 5: Pelletier SW. Academic Press; New York: 1987. p.55-132

<A NAME="RF21310SS-2">2</A> Suffness M. Cordell GA. In The Alkaloids: Chemistry and Pharmacology Vol. 25: Brossi A. Academic Press; Orlando: 1985. p.3-355

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

<A NAME="RF21310SS-4">4</A> Gao W. Lam W. Zhong S. Kaczmarek C. Baker DC. Cheng YC. Cancer Res. 2004, 64: 678

<A NAME="RF21310SS-5A">5a</A> An T.-Y. Huang R.-Q. Yang Z. Zhang D.-K. Li G.-R. Yao Y.-C. Gao J. Phytochemistry 2001, 58: 1267

<A NAME="RF21310SS-5B">5b</A> Wang QM, Wang KL, Huang ZQ, Liu YX, Li H, Hu TS, Jin Z, Fan ZJ, and Huang RQ. inventors; CN 101189968. ; Chem. Abstr. 2008, 149, 97630

For the most recent examples, see:

<A NAME="RF21310SS-6A">6a</A> Kim S. Lee J. Lee T. Park HG. Kim D. Org. Lett. 2003, 5: 2703

<A NAME="RF21310SS-6B">6b</A> Kim S. Lee T. Lee E. Lee J. Fan GJ. Lee SK. Kim D. J. Org. Chem. 2004, 69: 3144

<A NAME="RF21310SS-6C">6c</A> Furstner A. Kennedy JW. Chem. Eur. J. 2006, 12: 7398

<A NAME="RF21310SS-6D">6d</A> Kim S. Lee YM. Lee J. Lee T. Fu Y. Song Y. Cho J. Kim D. J. Org. Chem. 2007, 72: 4886

<A NAME="RF21310SS-6E">6e</A> Zeng W. Chemler SR. J. Org. Chem. 2008, 73: 6045

<A NAME="RF21310SS-6F">6f</A> McIver A. Young DD. Deiters A. Chem. Commun. 2008, 39: 4750

<A NAME="RF21310SS-6G">6g</A> Yamashita S. Kurono N. Senboku H. Tokuda M. Orito K. Eur. J. Org. Chem. 2009, 1173

<A NAME="RF21310SS-6H">6h</A> Rossiter LM. Slater ML. Giessert RE. Sakwa SA. Herr RJ. J. Org. Chem. 2009, 74: 9554

<A NAME="RF21310SS-6I">6i</A> Stoye A. Opatz T. Org. Lett. 2010, 12: 214

<A NAME="RF21310SS-6J">6j</A> Yang XM. Shi Q. Bastow KF. Lee KH. Org. Lett. 2010, 12: 1416

<A NAME="RF21310SS-6K">6k</A> Ambrosini LM. Cernak TA. Lambert TH. Tetrahedron 2010, 66: 4882

<A NAME="RF21310SS-7">7</A> Wang ZW. Li Z. Wang KL. Wang QM. Eur. J. Org. Chem. 2010, 292

<A NAME="RF21310SS-8">8</A> Wang ZW. Wang QM. Tetrahedron Lett. 2010, 51: 1377

<A NAME="RF21310SS-9A">9a</A> Bradsher CK. Hunt DA. J. Org. Chem. 1981, 46: 327

<A NAME="RF21310SS-9B">9b</A> Parham WE. Bradsher CK. Acc. Chem. Res. 1982, 15: 300

<A NAME="RF21310SS-9C">9c</A> Collado MI. Lete E. Sotomayor N. Villa MJ. Tetrahedron Lett. 1995, 51: 4701

<A NAME="RF21310SS-9D">9d</A> Collado MI. Sotomayor N. Villa MJ. Lete E. Tetrahedron Lett. 1996, 37: 6193

<A NAME="RF21310SS-9E">9e</A> Collado MI. Manteca I. Sotomayor N. Villa MJ. Lete E. J. Org. Chem. 1997, 62: 2080

<A NAME="RF21310SS-9F">9f</A> Ardeo A. Lete E. Sotomayor N. Tetrahedron Lett. 2000, 41: 5211

<A NAME="RF21310SS-9G">9g</A> Ruiz J. Sotomayor N. Lete E. Org. Lett. 2003, 5: 1115

<A NAME="RF21310SS-9H">9h</A> Moreau A. Couture A. Deniau E. Grandclaudon P. Eur. J. Org. Chem. 2005, 3437

<A NAME="RF21310SS-9I">9i</A> Ruiz J. Ardeo A. Ignacio R. Sotomayor N. Lete E. Tetrahedron 2005, 61: 3311

<A NAME="RF21310SS-9J">9j</A> Ruiz J. Lete E. Sotomayor N. Tetrahedron 2006, 62: 6182

<A NAME="RF21310SS-9K">9k</A> Lamblin M. Couture A. Deniau E. Grandclaudon P. Tetrahedron 2007, 63: 2664

Supplementary Material

Supporting Information