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

Abstract

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. © 2002 Elsevier Science Ltd. All rights reserved.