A new route to β-keto-δ-lactones: Practical preparation of (R)-3-hexyl-5,6-dihydro-4-hydroxy-6-undecyl-2H-pyran-2-one, a key intermediate in the asymmetric synthesis of tetrahydrolipstatin

Article abstract of DOI:10.1016/S0040-4039(00)60566-X

A formal asymmetric synthesis of the anti-obesity drug tetrahydrolipstatin is reported. The advanced intermediate (R)-3-hexyl-5,6-dihydro-4-hydroxy-6-undecyl-2H-pyran-2-one is prepared in a brief sequence using a novel cyclization reaction. The sequence is also used to prepare other β-ketolactones.