Synthesis of penta-N-protected thermopentamine and its selective deprotection

Tetrahedron

Volumn 54, Issue 28, 1998, Pages 8035-8046

  Pak, Jae Kyoung ^a   Guggisberg, Armin ^a   Hesse, Manfred ^a  

^a Organisch chemisches Institut Universität   (Switzerland)

Author keywords

Alkaloids; Polyamines; Protecting groups

Indexed keywords

POLYAMINE; TERT BUTYL N [N' (TRIMETHYLSILYLETHANESULFONYL) 3 AMINOPROP 1 YL]CARBAMATE; UNCLASSIFIED DRUG;

ARTICLE; ISOLATION PROCEDURE; PRIORITY JOURNAL; REACTION ANALYSIS; REDUCTION; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0032499975     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/s0040-4020(98)00442-6     Document Type: Article

References (16)

1. [1] Guggisberg A, Hesse M.: Natural polyamine derivatives-New aspects of their isolation, structure elucidation and synthesis. In: Cordell G, Brossi A, editors. The Alkaloids. Vol 50. Orlando: Academic Press Inc., 1998: 219-256.
2. [2] Hamana K, Niitsu M, Samejima K, Matsuzaki S. FEMS Microbiology Lett. 1990; 68: 27-30.
3. [3] Hamana K, Hamana H, Niitsu M, Samejima K, Itoh T. Microbios. 1996; 85: 19-33.
4. [4] Jasys VJ, Kelbaugh PR, Nason DM, Phillips D, Rosnack KJ, Saccomano NA, Stroh JG, Volkmann RA. J. Am. Chem. Soc. 1990; 112: 6696-6704.
5. [5] Yu H, Rosen MK, Saccomano NA, Phillips D, Volkmann RA, Schreiber SL. Biochemistry. 1993; 32: 13123-13129.
6. [6] Usherwood PNR, Blagbrough IS. Pharmac. Ther. 1991; 52: 245-268
7. [7] Bergeron RJ, Hawthorne TR, Vinson JRT, Beck DE Jr, Ingeno MJ. Cancer Research. 1989; 49: 2959-2964.
8. [8] Kovàcs L, Hesse M. Helv. Chim. Acta. 1992; 75: 1909-1924.
9. [9] Chiba T, Akizawa T, Matsukawa M, Kawai N, Kono Y, Yoshioka M. Chem. Pharm. Bull. 1997; 45(1): 93-100.
10. [10] Goulaouic-Dubois C, Guggisberg A, Hesse M. Tetrahedron. 1995; 51(46): 12573-12582.
11. [11] Garro-Helion F, Merzouk A, Guibé F. J. Org. Chem. 1993; 58: 6109-6113.
12. [12] Hasegawa E, Curran DP. J. Org. Chem. 1993; 58: 5008-5010.
13. [13] Ward DE, Gai Y, Kaller BF. J. Org. Chem. 1996; 61: 5498-5505.
14. [14] Goulaouic-Dubois C, Guggisberg A, Hesse M. J. Org. Chem. 1995; 60: 5969-5972.
15. [15] Karpcho AP, Kuell CS. Synth. Commun. 1990; 20(16): 2559-2564.
16. [16] Ando T, Yamawaki J. Chem. Lett. 1979: 45-46.