An expeditious enantioselective synthesis of antimycin A3b.
A straightforward enantioselective route to (+)-antimycin A3b is presented, which used a TiCl4-mediated asymmetric aldolization to construct C-7/C-8 and BnOH/DMAP to remove the chiral auxiliary with concurrent protection of the carboxylic group, respectively. Closing the dilactone ring was achieved in 62% yield (previously 0.8%, 13.4%, or 20%) in the presence of the C-8 ester functionality. The overall yield (34.5%) was significantly higher than that (0.019-3.6%) of the earlier routes.
Wu
Yikang
Y
State Key Laboratory of Bio-organic & Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, China. yikangwu@mail.sioc.ac.cn
Yang
Yong-Qing
YQ
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D000968:Antimycin A / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D018942:Macrolides / Q000138:chemical synthesis*; D015394:Molecular Structure
D000900:Anti-Bacterial Agents; D018942:Macrolides; D000968:Antimycin A; C520124:antimycin A3b