Synthetic studies on altemicidin: stereocontrolled construction of the core framework.
The stereoselective synthesis of the key intermediate for altemicidin has been accomplished. The synthesis commenced with a bicyclo[3.3.0] framework, which was readily obtained via an intramolecular C-H insertion reaction. A Curtius rearrangement was employed as a key step to stereoselectively construct the beta-hydroxyl alpha-disubstituted-alpha-amino acid structure. Synthesis of vinylogous urea was achieved using hydrolysis of nitrile intermediate.
Kan
Toshiyuki
T
School of Pharmaceutical Sciences, University of Shizuoka and COE Program in the 21st century, 52-1 Yada, Suruga-ku, Shizuoka 422-8526, Japan. kant@u-shizuoka-ken.ac.jp
Kawamoto
Yuichiro
Y
Asakawa
Tomohiro
T
Furuta
Takumi
T
Fukuyama
Tohru
T
D039903:Actinobacteria / Q000737:chemistry; D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013457:Sulfur Compounds / Q000138:chemical synthesis* / Q000737:chemistry
D000470:Alkaloids; D009570:Nitriles; D011725:Pyridines; D013457:Sulfur Compounds; C061865:altemicidin