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Biologically active glycosides from asteroidea, XV. Asymmetric synthesis of phytosphingosine and phytosphingosine anhydro base: Assignment of the absolute stereochemistry
Author(s) -
Sugiyama Shigeo,
Honda Masanori,
Komori Tetsuya
Publication year - 1988
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.198819880702
Subject(s) - chemistry , stereochemistry , absolute configuration , two dimensional nuclear magnetic resonance spectroscopy , glycoside
The first asymmetric synthesis of a phytosphingosine, (2 S ,3 S ,4 R )‐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.