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Haterumadysins A-D, sesquiterpenes from the Okinawan marine sponge Dysidea chlorea
Katsuhiro Ueda1, Takashi Kadekaru, Eric R O Siwu
1Department of Chemistry, Biology and Marine Sciences, University of the Ryukyus, Nishiharacho, Okinawa 903-0213, Japan. kueda@sci.u-ryukyu.ac.jp
Abstract:
Haterumadysins A-D (1-4) and two known compounds, spirodysin (5) and dehydroherbadysinolide (6), were isolated from the sponge Dysidea chlorea. Their structures were successfully determined by detailed spectroscopic analysis. Compounds 1-5 all showed the ability to inhibit the division of fertilized sea urchin eggs.
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Characteristics of the diene
Conformation
The simplest example of a diene is 1,3-butadiene, an acyclic conjugated π system. At room temperature, the molecule exists as a mixture of s-cis and s-trans conformers by virtue of rotation around the carbon–carbon single bond. Although the s-trans isomer is more stable, the...
Prochirality
Stability of Conjugated Dienes
A comparison of the enthalpies of hydrogenation of dienes reveals that conjugated dienes release less heat on hydrogenation, rendering them more stable than their nonconjugated analogs.
Structure of Conjugated Dienes
Conjugated dienes are compounds characterized by the presence of alternating double and single bonds. In a conjugated system like 1,3-butadiene, the unhybridized 2p orbital on each carbon overlaps continuously, allowing the π electrons to be delocalized across the entire molecule. In contrast, this type of overlap does not occur in cumulated and isolated dienes, such as 2,3-pentadiene and 1,4-pentadiene, respectively. Instead, the π electrons remain localized between the double...