A new diorganozinc-based enantioselective access to truncated d-ribo-phytosphingosine

The use of a trans α,β-epoxyaldehyde as a precursor of d-ribo-phytosphingosines was studied. The highly stereoselective alkylation of the aldehyde with a diorganozinc reagent was ensured through double asymmetric induction. The regioselective opening of the epoxide in turn gives access to an azide from which a C10 phytosphingosine can be easily prepared.