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oai:figshare.com:article/32633145 2026-10-01T17:05:44Z portal_1172 item_type_8 month_year_10_2026

Total synthesis of (+)-trichostatins A and C via the O-directed dialkylacetylene free radical hydrostannation reaction Ke Pan (200562) PUREID: 346574975 total synthesis Trichostatin C O-directed free radical hydrostannation (+)-Trichostatin A (TSA) is a naturally-occurring histone deacetylase (HDAC) inhibitor of type I, II, and IV HDACs that exhibits powerful anticancer effects. (+)-Trichostatin C (TSC) is natural glucopyranosyl hydroxylamine derivatives of TSA with O-β-D-glucopyranosylhydroxylamine. We became interested in developing an enantioselective total synthesis of the (+)-TSA and (+)-TSC molecule to potentially show off the significant utility of the O-directed free radical hydrostannation of disubstituted alkynes for constructing trisubstituted alkenes in target molecules that contain a dialkylaniline ring system. Such a synthetic approach to (+)-TSA might potentially be adaptable to the creation of novel analogues that could be screened for their HDAC inhibitory effects, which are of potential therapeutic relevance to the treatment of diseases ranging from cancer right through to SARS-CoV-2 (COVID-19). Our new total syntheses of (+)-trichostatins A and C have been completed in high optical purity (97% ee), so confirming that the O-directed free radical hydrostannation with Ph3SnH/cat. Et3B can be successfully applied in dialkylaniline-containing dialkyl acetylene systems. With this new route, many novel avenues of the trichostatins can potentially be prepared and screened.<br> 2026-10-01T17:05:44Z Text Thesis 10.17034/32633145.v1 https://figshare.com/articles/thesis/Total_synthesis_of_-trichostatins_A_and_C_via_the_O-directed_dialkylacetylene_free_radical_hydrostannation_reaction/32633145 All Rights Reserved