- Synthesis of Benzo[ b]furans by Intramolecular C-O Bond Formation Using Iron and Copper Catalysis
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One-pot processes for the synthesis of benzo[b]furans from 1-aryl- or 1-alkylketones using nonprecious transition metal catalysts have been developed. Regioselective iron(III)-catalyzed halogenation of the aryl ring, followed by iron- or copper-catalyzed O-arylation allowed the synthesis of various structural analogues, including the benzo[b]furan-derived natural products corsifuran C, moracin F, and caleprunin B.
- Henry, Martyn C.,Sutherland, Andrew
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p. 2766 - 2770
(2020/03/30)
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- Enantioselective reduction of β-keto acids with engineered streptomyces coelicolor
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Compelling evidence for the intermediacy of the free β-keto acid 1, rather than the corresponding enzyme-bound thiolate as previously proposed, in the biosynthesis of the antibiotic actinorhodin (2) was obtained from studies of the enantioselective reduction of a range of β-keto acids by the engineered strain of S. coelicolor CH999/pIJ5675. This excellent whole-cell biotransformation system gave the desired S β-hydroxy acids with >95% ee.
- Booker-Milburn, Kevin I.,Gillan, Rebecca,Kimberley, Meriel,Taguchi, Takaaki,Ichinose, Koji,Richard Stephenson,Ebizuka, Yutaka,Hopwood, David A.
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p. 1121 - 1125
(2007/10/03)
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- Two general routes to 1,4-disubstituted-2,3,4,5-tetrahydro- 1H-3-benzazepines.
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[structure] Two general routes to 1,4-disubstituted-2,3,4, 5-tetrahydro-1H-3-benzazepines are described. Both routes utilize an appropriately functionalized phenethylamino alcohol as the penultimate intermediate: the first route makes use of the reductive amination of a benzyl alkyl ketone with alpha-(aminomethyl)benzyl alcohol, while the second route utilizes the addition of a Grignard reagent to the oxazolidine derived from a substitued phenylacetaldehyde and alpha-(methylaminomethyl)benzyl alcohol. In all cases studied, the cis-1,4-disubstituted-2,3,4, 5-tetrahydro-1H-3-benzazepine was obtained as the major product.
- Gerritz,Smith,Nanthakumar,Uehling,Cobb
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p. 4099 - 4102
(2007/10/03)
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- SYNTHESIS OF METABOLIC INTERMEDIATES OF DIETHYLSTILBESTROL
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This report details the synthesis of 1) 3,4,4'-trihydroxy-α,α'-diethyl-trans-stilbene; 2) 3,4-bis-(p-hydroxyphenyl)-trans-3-hexenol; 3) 3,4-bis-(p-hydroxyphenyl)-2,4-cis,cis-hexadienol; 4) 3,4-bis-(3'-methoxy-4'-hydroxyphenyl)-trans-3-hexene; 5) 3,4-bis-(3',4'-dimethoxyphenyl)-trans-3-hexene.These compounds are suspected metabolites of diethylstilbestrol.
- Hill, Kenneth A.,Peterson, Dorothy M.,Damodaran, Kalyani M.,Rao, P. Narasimha
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p. 327 - 344
(2007/10/02)
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