A Simple Stereoselective Synthesis of a Novel Cytotoxic Alkaloid Barrenazine A [¹]

Abstract

The cytotoxic marine alkaloid barrenazine A was synthesized stereoselectively in eight simple steps from octanal. A key step involved the preparation of a functionalized 4- aminopiperidin-5-ol that underwent oxidative dimerization on treatment with 2-iodoxybenzoic acid.

alkaloids - stereoselective synthesis - dimerizations - cytotoxins

References

1

Part 47 in the series Synthetic Studies on Natural Products.

2 Chill L. Aknin M. Kashman Y. Org. Lett.  2003,  5:  2433 

3a Focken T. Charette AB. Org. Lett.  2006,  8:  2985 

3b Montserrat Martinez M. Sarandeses LA. Pérez Sestelo J. Tetrahedron Lett.  2007,  48:  8536 

3c Buron F. Turck A. Plé N. Bischoff L. Marsais F. Tetrahedron Lett.  2007,  48:  4327 

3d Peña-López M. Montserrat Martínez M. Sarandeses LA. Pérez Sestelo J. Org. Lett.  2010,  12:  852 

4a Das B. Krishnaiah M. Sudhakar Ch. Bioorg. Med. Lett.  2010,  20:  2303 

4b Das B. Veeranjaneyulu B. Balasubramanyam P. Srilatha M. Tetrahedron: Asymmetry  2010,  21:  2762 

4c Das B. Kumar DN. Tetrahedron Lett.  2010,  51:  6011 

5 Hanava H. Hashimoto T. Maruoka K. J. Am. Chem. Soc.  2003,  125:  1708 

6a Chattarjee AK. Morgan JP. Scholl N. Grubbs RH. J. Am. Chem. Soc.  2000,  122:  3783 

6b Trnka TM. Grubbs RH. Acc. Chem. Res.  2001,  34:  18 

7 Coombs TC. Lushington GH. Douglas J. Aube J. Angew. Chem. Int. Ed.  2011,  50:  2734 

8 Fürst A. Plattner PA. Helv. Chim. Acta  1949,  32:  275 

9a Nicolaou KC. Mathison CJN. Montagnon T. Angew. Chem. Int. Ed.  2003,  42:  4077 

9b Fontaine P. Chiaroni A. Massou G. Zhu J. Org. Lett.  2008,  10:  1509