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Modular Total Syntheses of the Marine-Derived Resorcylic Acid Lactones Cochliomycins A and B Using a Late-Stage Nozaki–Hiyama–Kishi Macrocyclization Reaction
- Bolte, Benoit, Basutto, Jose A., Bryan, Christopher
S., Garson, Mary J., Banwell, Martin G., Ward, Jas S.
- Journal of organic chemistry 2015 v.80 no.1 pp. 460-470
- chemical structure, hydrolysis, lactones, olefin, organic chemistry
- The natural products cochliomycin A (1) and cochliomycin B (2), two resorcylic acid lactones obtained from marine sources, have been prepared in a concise and stereocontrolled manner from the readily accessible building blocks 4–6. Olefin cross-metathesis, trans-esterification and Nozaki–Hiyama–Kishi (NHK) macrocyclization reactions were employed in the key steps. Hydrolysis of the immediate precursor to cochliomycin B affords the resorcylic acid lactone zeaenol (24).