Liebigs Annalen der Chemie

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

K Mori, K Uenishi

Index: Mori, Kenji; Uenishi, Keiji Liebigs Annalen der Chemie, 1994 , # 1 p. 41 - 48

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Citation Number: 13

Abstract

Abstract Symbioramide [(2S, 2′ R, 3R, 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 (2S, 2′ S, 3R, 3′ E)-isomer 28 of 1 was also synthesized to further confirm the structure of 1.