Phytochemistry p. 529 - 532 (1997)
Update date:2022-08-25
Topics:
Kajiwara, Tadahiko
Akakabe, Yoshihiko
Matsui, Kenji
Kodama, Kazuya
Koga, Harunobu
Nagakura, Takamitsu
(-)-(3R,4R)-3-Butyl-4-vinylcyclopentene [(-)-1] was synthesized via (+)- (1S,5R)-3-oxabicyclo [3,3,0] oct-6-en-2-one. Synthetic (-)-1 coincided with the peak with later retention time of racemic (+)-1 in a chiral GC (CP- Cyclodex 236M), while the natural 1 in essential oils from the marine brown algae, Dictyopteris prolifera and D. sp. was identical with the earlier retention time peak. Thus, the absolute configuration of the natural product in Dictyopteris oils was determined as (+)-(3S,4S) with ca 100% enantiomeric excess.
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