Synthesis of obscuraminol A using an organocatalyzed enantioselective Henry reaction
The first synthesis of the polyunsaturated amino alcohol natural product obscuraminol A is
reported. This stereoselective synthesis was based on an anti-and enantioselective
organocatalyzed Henry reaction followed by a chemoselective SmI 2-mediated reduction
that affected only the nitro-group of the Henry product. These efforts yielded obscuraminol A
where the configuration of the all-Z skipped double bonds was conserved from the starting
material, ie. the ethyl ester of (all-Z)-eicosa-5, 8, 11, 14, 17-pentaenoic acid. Our synthesis …
reported. This stereoselective synthesis was based on an anti-and enantioselective
organocatalyzed Henry reaction followed by a chemoselective SmI 2-mediated reduction
that affected only the nitro-group of the Henry product. These efforts yielded obscuraminol A
where the configuration of the all-Z skipped double bonds was conserved from the starting
material, ie. the ethyl ester of (all-Z)-eicosa-5, 8, 11, 14, 17-pentaenoic acid. Our synthesis …
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