Synthesis of glycocinnasperimicin D.
Chemistry
; 16(2): 600-10, 2010 Jan 11.
Article
in En
| MEDLINE
| ID: mdl-19937620
ABSTRACT
The first total synthesis of amino sugar antibiotic glycocinnasperimicin D (1) has been achieved by a convergent, three-component coupling strategy. The key steps involve the Heck-Mizoroki reaction by using the iodophenyl glycoside 50 and acryl amide 32 to furnish the right core structure of 1, and the construction of the urea glycoside employing the reaction of glycosyl isocyanate 8 with amino sugar 9. Glycosyl isocyanate 8 was prepared by the oxidation of isonitrile 10, which displayed excellent reactivity in the coupling event. Synthetic roadblocks, encountered during this synthetic effort, have led to the development of the alpha-selective, Lewis acid catalyzed phenyl glycosylation process with 2-amino-hexopyranose and a procedure for acetonide deprotection without affecting the silyl ethers.
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Main subject:
Anti-Bacterial Agents
Language:
En
Journal:
Chemistry
Journal subject:
QUIMICA
Year:
2010
Document type:
Article
Affiliation country:
Japón