Stereoselective synthesis of pamamycin-607.
A macrodiolide antibiotic pamamycin-607 was synthesized by joining two hydroxy acid components. Three cis-2, 5-disubstituted tetrahydrofuran rings in the molecule were stereoselectively prepared by radical cyclization reactions of beta-alkoxyvinyl ketone intermediates and a beta-alkoxymethacrylate substrate. The key step of the synthesis is characterized by the predominant threo product formation in the radical cyclization reaction of a beta-alkoxymethacrylate intermediate.
Jeong
Eun Jeong
EJ
School of Chemistry and Molecular Engineering, Seoul National University, Seoul 151-747, Korea.
Kang
Eun Joo
EJ
Sung
Lee Taek
LT
Hong
Sung Kil
SK
Lee
Eun
E
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D000935:Antifungal Agents / Q000138:chemical synthesis*; D018942:Macrolides; D009930:Organic Chemicals; D013237:Stereoisomerism; D013302:Streptomyces / Q000737:chemistry
D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D018942:Macrolides; D009930:Organic Chemicals; C470905:pamamycin-607; C024500:pamamycin