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Asymmetric Total Synthesis of (−)-(3R)‑Inthomycin C

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journal contribution
posted on 04.06.2018, 14:26 by Sandra Balcells, Maxwell B. Haughey, Johannes C. L. Walker, Laia Josa-Culleré, Christopher Towers, Timothy J. Donohoe
A short (10 step) and efficient (15% overall yield) synthesis of the natural product (−)-(3R)-inthomycin C is reported. The key steps comprise three C–C bond-forming reactions: (i) a vinylogous Mukaiyama aldol, (ii) an olefin cross-metathesis reaction, and (iii) an asymmetric Mukaiyama–Kiyooka aldol. This route is notable for its brevity and has the advantage of lacking stoichiometric tin-promoted cross-coupling reactions present in previous approaches. Initial investigations on the biological activity of (−)-(3R)-inthomycin C and structural analogues on human cancer cell lines are also described for the first time.