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The first plant-like biosynthesis of benzoic acid in a prokaryote, the marine actinomycete 'Streptomyces maritimus', has been characterized. Feeding experiments with 2 H- and 13 C-labeled intermediates revealed that phenylalanine is metabolized to benzoyl-coenzyme A (CoA) by means of a phenylalanine ammonia lyase and subsequent β-oxidation of cinnamoyl-CoA. Benzoyl-CoA serves...
An efficient and highly diastereoselective synthesis of lamoxirene (cis-2-cyclohepta-2,5-dienyl-3-vinyloxirane, 4), the gamete releasing and -attracting pheromone of the Laminariales (Phaeophyceae), is reported. Ethyl cyclohepta-2,5-diene carboxylate (7) is effectively alkylated to provide the syn-α-chlorohydrin 8 via reductive chloroallylboration with DIBAL-H and (Z)-γ-chloroallyl-BBN. Cyclisation...
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