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Total synthesis of prolycopene
Affiliation:1. Department of Chemical Engineering, Faculty of Engineering, University of Isfahan, Isfahan, I.R, Iran;2. Department of Nanotechnology, Faculty of Advanced Science and Technologies, University of Isfahan, Isfahan, I.R, Iran;3. Department of Chemical Engineering, University of Waterloo, Waterloo, Canada
Abstract:A total synthesis of the tetra-Z-isomer (1, ‘prolycopene’) of lycopene found in fruits of the Tangerine tomatoLycopersicon esculentum, based on: (i) elaboration of the2Z, 6E-carbinol (4) from a Pd-coupling reaction between the vinyl bromide (2) and the Z-enynol(3) (ii) successive Wittig reactions between (6) and (7), [leading to (8)] and between (8) and (6), and (iii) partial catalytic hydrogenation of thebis-acetylene (9), is described.
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