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

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公開日
1988-07-14
権利情報
  • http://onlinelibrary.wiley.com/termsAndConditions#vor
DOI
  • 10.1002/jlac.198819880702
公開者
Wiley

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

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