Synthesis and biological evaluation of (+/-)-dinemasone C and analogues.
Dinemasone C was prepared in three steps (8% overall yield) from cis-tetrahydro-4-hydroxy-6-methyl-2-pyrone by aldol reaction with 2,4-hexadienal, epoxidation followed by cyclization, and epimerization of the ring fusion. Dinemasone C, epi-dinemasone C, anhydrodinemasone BC, and nor-dinemasone B are active against bacteria, including Legionella pneumophila Corby, algae, and fungi.
Stewart
Amie M
AM
Department of Chemistry MS 015, Brandeis University, Waltham, Massachusetts 02454-9110, USA.
Meier
Kathrin
K
Schulz
Barbara
B
Steinert
Michael
M
Snider
Barry B
BB
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D001410:Bacillus megaterium / Q000187:drug effects; D001487:Basidiomycota / Q000187:drug effects; D002708:Chlorella / Q000187:drug effects; D003500:Cyclization; D004926:Escherichia coli / Q000187:drug effects; D006574:Heterocyclic Compounds, 2-Ring / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D016952:Legionella pneumophila / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D008968:Molecular Conformation; D013237:Stereoisomerism
D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D006574:Heterocyclic Compounds, 2-Ring; C553863:dinemasone C