Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 68, Issue 7, Pages 2760-2764Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo0268916
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An efficient and practical synthesis of alpha-methylomuralide (3), a selective inhibitor of proteasomes, has been developed as outlined in Scheme 1. Among the advantages of this route of synthesis over previously described approaches are (1) ease of scale-up and (2) high yields (28% overall yield of a-methylomuralide from 6) and stereocontrol (including high enantiocontrol). The synthesis is well suited to the production of 3 in the quantities needed for material-intensive in vivo investigations.
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