Biomimetic Conversion of (3S)-(–)-Neodictyoprolenol to Optically Pure (1S,2R)-(–)-Dictyopterene B, Marine Algal Sex Pheromone

Both enantiomers of (3S)-(-)- and (3R)-(+)-Neodictyoprolenol [(3S,5Z,8Z)-(-)-1,5,8-unde-catrien- 3-ol] were successfully converted to the algal sex pheromone, (1S,2R)-(-)-dictyopterene B and (1R,2S)-(+)-dictyopterene B in high enantiomeric purities (e.e. > 99%), respectively, by the biomimetic re...

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Published inZeitschrift für Naturforschung C. A journal of biosciences Vol. 58; no. 1; pp. 109 - 112
Main Authors Kajiwara, Tadahiko, Yamamoto, Yuuko, Akakabe, Yoshihiko, Matsui, Kenji, Shimizu, Hiroshi, Kawai, Tesuo
Format Journal Article
LanguageEnglish
Published Germany Verlag der Zeitschrift für Naturforschung 01.01.2003
Subjects
Biomimetic Conversion
Fatty Alcohols - chemical synthesis
Fatty Alcohols - chemistry
Fatty Alcohols - isolation & purification
Indicators and Reagents
Japan
Marine Algae
Phaeophyceae - chemistry
Pheromones
Sex Attractants - chemical synthesis
Sex Attractants - chemistry
Sex Attractants - isolation & purification
Stereoisomerism
Japan
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Summary:Both enantiomers of (3S)-(-)- and (3R)-(+)-Neodictyoprolenol [(3S,5Z,8Z)-(-)-1,5,8-unde-catrien- 3-ol] were successfully converted to the algal sex pheromone, (1S,2R)-(-)-dictyopterene B and (1R,2S)-(+)-dictyopterene B in high enantiomeric purities (e.e. > 99%), respectively, by the biomimetic reaction involving phosphorylation and elimination under a mild condition
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:0939-5075
1865-7125
DOI:10.1515/znc-2003-1-219