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Synthesis of sphingosine relatives, XIV. A new synthesis of symbioramide, a Ca ++ ‐ATPase activator from Symbiodinium sp.
Author(s) -
Mori Kenji,
Uenishi Keiji
Publication year - 1994
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.199419940109
Subject(s) - sphingosine , chemistry , stereochemistry , activator (genetics) , biochemistry , gene , receptor
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 .