Reagents for Bromination; Application in the Synthesis of Diterpenes, Sesquiterpenes and Bioactive Compounds

Author(s): Po S. Poon, Ajoy K. Banerjee, William J. Vera, Liadis Bedoya

Journal Name: Current Organic Chemistry

Volume 21 , Issue 10 , 2017


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Abstract:

Several organic compounds especially cyclic compounds containing double or triple bond and carbonyl compounds, aromatic compounds were brominated by employing several well-known reagents e.g., Nbromosuccinimide, bromine in acetic acid, ammonium bromide, hydrogen peroxide in acetic acid, carbon tetrabromide, phosphorous tribromide, 2,4,4,6-tetrabromocyclohex-2,5-dienone. The resulting compounds were utilized for the synthesis of several sesquiterpenes e.g., eudes-4(14)7(11)-diene-8-one, glutinosone, platyphyllide, occidentalol, drim-8-ene-7-one, cacalol, elemol, bakkenolide A, 10-bromo-α-chamigrene, allolaurintero, aplysin, costunolide, humulene, bisabollenes, bicycloelemene, occidol, longifolin, juvabiols, futronolide, etc. The importance of some of the mentioned reagents for bromination was also observed during the synthesis of the plant hormone abscisic acid, marine terpene synderol and α-asarone, a substance of potent hypolipidemic activity. The compounds obtained by bromination were likewise utilized for the synthesis of diterpenes like taxodione, spat-13,17- dien-5-ol and gibberellin A12. Some of these bromo compounds were utilized for the synthesis of many substituted tetralones, tetralins and naphthalenes e.g., 6,7-dimethoxy-2-tetralone, 8-methyl-7-methoxy-1-tetralone, 8- methyl-1-tetralone, 1,4-dimethoxy-1-acetylnaphthalene, 7-methoxy-1-naphthylacetic acid, 5,6-dimethoxy- 1,2,3,4-tetrahydronaphthalene-2-carboxylic acid, 2-hydroxy-1,4-dimethoxynaphthalene which were utilized for the synthesis of many bioactive compounds.

Dedicated with profound regards to Dr. Michael Kolb, ex-editor of Synthetic Communications

Keywords: N-bromosuccinimide (NBS), bromine in acetic acid, carbon tetrabromide, ammoniun bromide, hydrogen peroxide, phosphorous tribromide, silver tetrafluoroborate, bromine.

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Article Details

VOLUME: 21
ISSUE: 10
Year: 2017
Published on: 29 March, 2017
Page: [889 - 907]
Pages: 19
DOI: 10.2174/1385272821666161201121344
Price: $58

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