Total synthesis of methymycin.
Methynolide and 10-epi-methynolide were synthesized from the necessary segments, which were prepared by the addition of Grignard reagents to the corresponding alpha-alkoxyketones utilizing 1,2-stereochemical selection based on Cram chelation control. Ring-closing metathesis, as the key reaction, was carried out to combine the segments for the synthesis of methynolide and 10-epi-methynolide. The total synthesis of methymycin was also achieved by the glycosylation of methynolide with the trichloroimidate derivative of D-desosamine.
Oh
Hong-Se
HS
Department of Chemistry, Chungbuk National University, Cheongju 361-763, Republic of Korea.
Xuan
Richeng
R
Kang
Han-Young
HY
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry
D000900:Anti-Bacterial Agents; D018942:Macrolides; C522940:methynolide; C008517:methymycin