aBio-Organic Science Division, Korea Research Institute of Chemical Technology, PO Box 107, Yusung, Taejon 305-606, South Korea
Abstract:
2-Azetidinones were smoothly transformed to unsaturated ketones through the ring opening of activated 2-azetidinone by phosphonate stabilized carbanion and subsequent Horner–Wadsworth–Emmons olefination of the resulting β-ketophosphonates with aldehydes. A formal synthesis of l-erythro-sphingosine and d-lyxo-phytosphingosine from readily available 2-azetidinone was established utilizing this methodology.