Asymmetric total synthesis of (−)-(3R)-inthomycin C

Asymmetric total synthesis of (−)-(3R)-inthomycin C

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...

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Bibliografische gegevens
Hoofdauteurs: Balcells, S, Haughey, M, Walker, J, Josa-Cullere, L, Towers, C, Donohoe, T
Formaat: Journal article
Gepubliceerd in: American Chemical Society 2018
Omschrijving
Samenvatting: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.

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