Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 10, Issue 22, Pages 4424-4432Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c2ob25122a
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- EPSRC
- AstraZeneca [GR/T18783/01]
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An optically active tetrahydroquinoline intermediate (5) was prepared in 8 steps from monoprotected ethylene glycol, using a Pd-catalysed aza-Michael reaction to induce chirality. This can be transformed into three Galipea alkaloids (angustureine, galipeine and cuspareine). The proximity of a benzyloxy group is found to exert profound effects in several steps of the synthesis.
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