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The chiral methylenedioxolanone 1 is readily available from (S)-lactic acid but it has not been used as a dipolarophile for 1,3-dipolar cycloaddition before. Diarylnitrones 2 add stereoselectively to give spiro adducts 3, and when these are subjected to flash vacuum pyrolysis at 440 °C, they eliminate ButCHO and CO2 as shown to give b-lactams 4 via an oxacarbene rearrangment.
The enantiomeric methylenedioxolanone 5, conveniently available from (R)-alanine,1 gives products 6 of the opposite enantiomeric series. Synthesis and FVP of the example 7 affords the advanced Ezetimibe precursor 8, thus completing a formal total synthesis of this important cholesterol-lowering drug.
