Synthesis of sphingosine relatives, XIV. A new synthesis of symbioramide, a Ca ++ ‐ATPase activator from Symbiodinium sp.

Symbioramide [(2 S ,2′ R ,3 R , 3′ E )‐ N ‐(2′‐hydroxy‐3′‐octadecenoyl)dihydrosphingosine, 1 ] was synthesized from D ‐ erythro ‐dihydrosphingosine ( 19 ) and ( R , E )‐2′‐ tert ‐butyldimethylsilyloxy‐3′‐octadecenoic acid ( 14 ), which was prepared from ( E )‐2‐octadecen‐1‐ol ( 4 ) by employing the Sharpless asymmetric epoxidation. The (2 S ,2′ S ,3 R ,3′ E )‐isomer 28 of 1 was also synthesized to further confirm the structure of 1 .