Journal
ORGANIC LETTERS
Volume 13, Issue 14, Pages 3564-3567Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol200964m
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Funding
- Ara Parseghian Medical Research Foundation (APMRF)
- National Science Foundation
- American Chemical Society
- University of Notre Dame
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [0833220] Funding Source: National Science Foundation
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Two concise, convergent syntheses of (+/-)-trichostatin A (1), a potent histone deacetylase inhibitor, have been accomplished. The key step in both is a Pd-catalyzed alpha-alkenylation reaction between ketone 2 and either dienyl bromide 3 or alkenyl bromide 9 using a modification of cross-coupling conditions described by Negishi and Hartwig. A brief investigation has shown the potential utility of a Ni-catalyzed version of this reaction. The overall synthetic routes are short and amenable to scaleup, providing access to trichostatin A via trichostatic acid as a direct precursor.
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