Total Synthesis of Caprazamycin A: Practical and Scalable Synthesis of syn-ß-Hydroxyamino Acids and Introduction of a Fatty Acid Side Chain to 1,4-Diazepanone.
J Am Chem Soc
; 141(21): 8527-8540, 2019 05 29.
Article
in En
| MEDLINE
| ID: mdl-31067040
ABSTRACT
The first total synthesis of caprazamycin A (1), a representative liponucleoside antibiotic, is described. Diastereoselective aldol reactions of aldehydes 12 and 25-27, derived from uridine, with diethyl isocyanomalonate 13 and phenylcarbamate 21 were investigated using thiourea catalysts 14 or bases to synthesize syn-ß-hydroxyamino acid derivatives. The 1,4-diazepanone core of 1 was constructed using a Mitsunobu reaction, and the fatty acid side chain was introduced using a stepwise sequence based on model studies. Notably, global deprotection was realized using palladium black and formic acid without hydrogenating the olefin in the uridine unit.
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Main subject:
Azepines
/
Uridine
/
Fatty Acids
/
Amino Acids
Language:
En
Journal:
J Am Chem Soc
Year:
2019
Document type:
Article
Affiliation country:
Japón