Biologically active glycosides from asteroidea, XV. Asymmetric synthesis of phytosphingosine and phytosphingosine anhydro base: Assignment of the absolute stereochemistry

The first asymmetric synthesis of a phytosphingosine, (2S,3S,4R)‐2‐amino‐1,3,4‐hexadecanetriol (2), was accomplished by kinetic resolution and asymmetric epoxidation. The absolute stereochemistry of the phytosphingosine from starfishes (Acanthaster planci and Asterina pectinifera) was established to be the same as for 2. The phytosphingosine anhydro base 19 was also asymmetrically synthesized, and the structure was determined on the basis of NMR analyses involving 2D‐COSY, NOESY, and difference NOE experiments.