The Total Synthesis of (±)-Pumiliotoxin-C preliminary communication

1975 ◽  
Vol 58 (2) ◽  
pp. 593-595 ◽  
Author(s):  
Wolfgang Oppolzer ◽  
Wolfgang Fröstl ◽  
Hans Peter Weber
Keyword(s):  
Total Synthesis ◽  
Preliminary Communication ◽  
Pumiliotoxin C

Zur Totalsynthese des Human-Big-Gastrins I und seines 32-Leucin-Analogons (Vorläufige Mitteilung) / Total Synthesis of Human Big Gastrin I and the 32-Leucine Analogue (Preliminary Communication)

1977 ◽  
Vol 32 (7-8) ◽  
pp. 495-506 ◽  
Author(s):  
E. Wünsch ◽  
G. Wendlberger ◽  
A. Hallett ◽  
E. Jaeger ◽  
S. Knof ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Building Blocks ◽  
Ion Exchange Chromatography ◽  
Exchange Chromatography ◽  
Protecting Groups ◽  
Side Chain ◽  
Tertiary Alcohols ◽  
Synthetic Product ◽  
Preliminary Communication ◽  
Final Purification

A new total synthesis of the tetratriacontapeptide amide corresponding to the proposed primary structure of human big gastrin I is described. The synthetic route was based on the preparation of six suitably protected fragments, related to sequence 28 - 34, 23 - 27, 21 - 22, 15-20, 9 - 14, and 1 - 8, to be used as building blocks for the total synthesis. The protecting groups were selected according to the Schwyzer-Wünsch strategy of maximum side chain protection based on tertiary alcohols, also for the imidazol function of histidine. Subsequent assembly of the six fragments by three different pathways using the highly efficient Wünsch-Weygand condensation procedure to ensure minimum racemization, followed by deprotection of the synthetic products via exposure to trifluoroacetic acid and final purification by ion-exchange chromatography on DEAE-Sephadex A-25 and partition chromatography on Sephadex G-25, led to human big gastrin I, homogeneous within the limits of the analytical methods used. The biological activity of the synthetic product proved to be 50 percent higher than that of human little gastrin I. The 32-leucine analogue of human big gastrin I was prepared in the same way.

A short stereospecific total synthesis of dl-pumiliotoxin C

1977 ◽  
Vol 18 (14) ◽  
pp. 1253-1256 ◽  
Author(s):  
Larry E. Overman ◽  
Peter J. Jessup
Keyword(s):  
Total Synthesis ◽  
Pumiliotoxin C

Total synthesis of -pumiliotoxin c hydrochloride and its crystal structure

1975 ◽  
Vol 16 (5) ◽  
pp. 323-326 ◽  
Author(s):  
Toshiro Ibuka ◽  
Yasuo Inubushi ◽  
Ikutaro Saji ◽  
Kiyoshi Tanaka ◽  
Norio Masaki
Keyword(s):  
Crystal Structure ◽  
Total Synthesis ◽  
Pumiliotoxin C
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