The Morita−Baylis−Hillman reaction involves the coupling of activated alkenes or alkynes and electrophiles under Lewis base catalysis and is a versatile reaction in organic synthesis for the formation of carbon−carbon bonds. In our study of the chemistry ynol ethers, we have observed that Morita−Baylis−Hillman adducts (β-hydroxyenoates) can be assembled in good overall yields by the sequential treatment of ethoxyethynyllithium with two different aldehydes or ketones in the presence of BF<sub>3°</sub>OEt<sub>2</sub> as a promoter. The usefulness of this method is demonstrated in the total synthesis of the α-alkylidene lactone natural products subamolide D and subamolide E. These substances have been shown to be DNA damaging agents capable of inducing apoptosis in cancer cells. The syntheses of subamolides D and E were achieved in six steps each and accomplished in 53% and 61% overall yields respectively.

Total synthesis of the α-alkylidene lactone natural products subamolides D and E

253rd National Meeting (2017)

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