Bioinspired Total Syntheses of Tricrilactones D and F, Crispatumine I, and 2,3- trans -Crispatumine I

The bioinspired total syntheses of tricrilactones D and F, crispatumine I, and 2,3-trans-crispatumine I are reported. The conserved lactone-fused 9/5/6 spirocyclic core of these products was constructed via a mild bioinspired one-pot three-component cascade of protrilactione A, the purported biosynthetic precursor. Variation of the aldehyde and β-ketolactone components enable access to both homo- and heterocoupled natural products, each in 13 steps (longest linear sequence).