Organic & Biomolecular Chemistry 2009-11-07

Total synthesis of methymycin.

Hong-Se Oh, Richeng Xuan, Han-Young Kang

Index: Org. Biomol. Chem. 7(21) , 4458-63, (2009)

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Abstract

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.