Late-stage divergent synthesis and antifouling activity of geraniol–butenolide hybrid molecules
Author(s) -
Hiroyoshi Takamura,
T. Ohashi,
Takahiro Kikuchi,
Noriyuki Endo,
Yuji Fukuda,
Isao Kadota
Publication year - 2017
Publication title -
organic and biomolecular chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.923
H-Index - 146
eISSN - 1477-0539
pISSN - 1477-0520
DOI - 10.1039/c7ob01160a
Subject(s) - butenolide , geraniol , chemistry , biofouling , stereochemistry , biochemistry , essential oil , food science , membrane
Hybrid molecules consisting of geraniol and butenolide were designed and synthesized by the late-stage divergent strategy. In the synthetic route, ring-closing metathesis was utilized for the construction of a butenolide moiety. A biological evaluation of the eight synthetic hybrid compounds revealed that these molecules exhibit antifouling activity against the cypris larvae of the barnacle Balanus (Amphibalanus) amphitrite with EC 50 values of 0.30-1.31 μg mL -1 . These results show that hybridization of the geraniol and butenolide structural motifs resulted in the enhancement of the antifouling activity.
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