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DOI: 10.1055/s-2007-968716
Synthesis of (6E)-2′-O-Methylmyxalamide D
Contributor(s):Philip Kocienski, Stewart EcclesThe Ohio State University, Columbus, USA
Total Synthesis of 2′-O-Methylmyxalamide D and (6E)-2′-O-Methylmyxalamide D
J. Am. Chem. Soc. 2007, 129: 3826-3827
Publication History
Publication Date:
24 July 2007 (online)
Key words
boronic acid formation - stannylcupration - hydrozirconation - Stille coupling - Suzuki coupling
Significance
(6E)-2′-O-Methylmyxalamide D was isolated from the myxobacterium Cystobacter fuscus and exhibits antibiotic and antifungal properties. This synthesis utilizes two palladium-catalyzed coupling reactions to elaborate the bis-metallated triene core E.
Comment
Stannylcupration of alkyne B followed by oxidation gave C which underwent a boryl-Takai olefination to give the bismetallated triene E. Subsequent palladium-catalyzed coupling reactions with F and then J yielded (6E)-2′-O-methylmyxalamide D. Vinyl iodide J was produced by hydrozirconation of alkyne I and reaction of the intermediate vinylzirconium species with iodine.