Studies on the total synthesis of streptazolin and its related natural products: first total synthesis of (+/-)-8alpha-hydroxystreptazolone.
The intramolecular Pauson-Khand reaction of 2-oxazolone derivatives with a suitable heptynyl appendage gave exclusively the corresponding 4-hydroxy-6-substituted-9-oxa-1-azatricyclo[6.2.1.0(5,11)]undec-5-ene-7,10-diones. On the basis of 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. In addition, (+/-)-7-epi-8alpha-hydroxystreptazolone was also synthesized.
Nomura
Izumi
I
Faculty of Pharmaceutical Sciences, Kanazawa University, Takara-machi 13-1, Kanazawa 920-0934, Japan.
Mukai
Chisato
C
D000480:Alkynes / Q000737:chemistry; D000890:Anti-Infective Agents / Q000138:chemical synthesis*; D001688:Biological Products / Q000138:chemical synthesis*; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis*; D007659:Ketones / Q000737:chemistry; D010080:Oxazoles / Q000737:chemistry; D010880:Piperidines / Q000138:chemical synthesis*; D013237:Stereoisomerism
C470643:8-hydroxystreptazolone; D000480:Alkynes; D000890:Anti-Infective Agents; D001688:Biological Products; D006575:Heterocyclic Compounds, 3-Ring; D007659:Ketones; D010080:Oxazoles; D010880:Piperidines; C428165:streptazolin