Total synthesis of (+/-)-8alpha-hydroxystreptazolone.
[reaction: see text] The intramolecular Pauson-Khand reaction of 2-oxazolone derivatives with a suitable pentynyl appendage exclusively gave the corresponding 4-hydroxy-6-substituted-9-oxa-1-azatricyclo[6.2.1.0(5,11)]undec-5-en-7,10-diones. Based on this newly developed Pauson-Khand reaction of 2-oxazolone-alkyne derivatives, the first total synthesis of (+/-)-8alpha-hydroxystreptazolone was accomplished in a highly stereoselective manner.
Nomura
Izumi
I
Faculty of Pharmaceutical Sciences, Kanazawa University, Takara-machi, Kanazawa 920-0934, Japan.
Mukai
Chisato
C
D000890:Anti-Infective Agents / Q000138:chemical synthesis / Q000737:chemistry; D003500:Cyclization; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D006358:Hot Temperature; D017953:Isocyanates / Q000737:chemistry; D008968:Molecular Conformation; D015394:Molecular Structure
C470643:8-hydroxystreptazolone; D000890:Anti-Infective Agents; D006571:Heterocyclic Compounds; D006575:Heterocyclic Compounds, 3-Ring; D017953:Isocyanates