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Monday, August 24 • 4:00pm - 4:20pm
[0144] Asymmetric synthesis of β-lactams by gas phase pyrolysis

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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.

ST Lecturers
avatar for Alan Aitken

Alan Aitken

Senior Lecturer, University of St Andrews
R Alan AitkenSenior LecturerSchool of ChemistryPurdie BuildingNorth HaughSt AndrewsKY16 9STUnited Kingdom

Monday August 24, 2015 4:00pm - 4:20pm PDT
UCEN State