Efficient enantioselective total synthesis of arabino-phytosphingosine

Abstract

Enantioselective total synthesis of arabino-phytosphingosine has been achieved in 8 steps employing Claisen rearrangement and Fleming-Tamao oxidation as key steps. Installation of all chiral centers present in arabino-phytosphingosine was achieved through the use of asymmetric catalysis. This synthesis provides one of the most efficient routes to prepare 2-amino- 1,3,4-triol moiety.