Convenient Synthesis of the Main Dehydrohexapeptide Skeleton Constituting a Macrocyclic Antibiotic, Berninamycin A.

ChemInform ◽  
2003 ◽  
Vol 34 (10) ◽  
Author(s):  
Hirohumi Saito ◽  
Takahiro Yamada ◽  
Kazuo Okumura ◽  
Yasuchika Yonezawa ◽  
Chun-gi Shin
1998 ◽  
Vol 71 (8) ◽  
pp. 1863-1870 ◽  
Author(s):  
Kazuo Okumura ◽  
Hiroyuki Saito ◽  
Chung-gi Shin ◽  
Kazuyuki Umemura ◽  
Juji Yoshimura

2004 ◽  
Vol 33 (1) ◽  
pp. 72-73 ◽  
Author(s):  
Tetsuya Kayano ◽  
Yasuchika Yonezawa ◽  
Chung-gi Shin

2002 ◽  
Vol 31 (11) ◽  
pp. 1098-1099 ◽  
Author(s):  
Hirohumi Saito ◽  
Takahiro Yamada ◽  
Kazuo Okumura ◽  
Yasuchika Yonezawa ◽  
Chung-gi Shin

ChemInform ◽  
2010 ◽  
Vol 29 (48) ◽  
pp. no-no
Author(s):  
K. OKUMURA ◽  
H. SAITO ◽  
C. SHIN ◽  
K. UMEMURA ◽  
J. YOSHIMURA

ChemInform ◽  
2004 ◽  
Vol 35 (16) ◽  
Author(s):  
Tetsuya Kayano ◽  
Yasuchika Yonezawa ◽  
Chung-gi Shin

2017 ◽  
Vol 68 (1) ◽  
pp. 180-185
Author(s):  
Adriana Maria Andreica ◽  
Lucia Gansca ◽  
Irina Ciotlaus ◽  
Ioan Oprean

Were developed new and practical synthesis of (Z)-7-dodecene-1-yl acetate and (E)-9-dodecene-1-yl acetate. The routes involve, as the key step, the use of the mercury derivative of the terminal-alkyne w-functionalised as intermediate. The synthesis of (Z)-7-dodecene-1-yl acetate was based on a C6+C2=C8 and C8+C4=C12 coupling scheme, starting from 1,6-hexane-diol. The first coupling reaction took place between 1-tert-butoxy-6-bromo-hexane and lithium acetylide-ethylendiamine complex obtaining 1-tert-butoxy-oct-7-yne, which is transformed in di[tert-butoxy-oct-7-yne]mercury. The mercury derivative was directly lithiated and then alkylated with 1-bromobutane obtaining 1-tert-butoxy-dodec-7-yne. After acetylation and reduction with lithium aluminium hydride of 7-dodecyne-1-yl acetate gave (Z)-7-dodecene-1-yl acetate with 96 % purity. The synthesis of (E)-9-dodecene-1-yl acetate was based on a C8+C2=C10 and C10+C2=C12 coupling scheme, starting from 1,8-octane-diol. The first coupling reaction took place between 1-tert-butoxy-8-bromo-octane and lithium acetylide-ethylendiamine complex obtaining 1-tert-butoxy-dec-9-yne, which is transformed in di[tert-butoxy-dec-9-yne]mercury. The mercury derivative was directly lithiated and then alkylated with 1-bromoethane obtaining 1-tert-butoxy-dodec-9-yne. After reduction with lithium aluminium hydride of 1-tert-butoxy-(E)-9-dodecene and acetylation was obtained (E)-9-dodecene-1-yl acetate with 97 % purity.


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