Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 33, Pages 9553-9556Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201602910
Keywords
biomimetic synthesis; configuration determination; lactams; total synthesis; vibrational spectroscopy
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Funding
- JSPS KAKENHI [15K07416]
- Grants-in-Aid for Scientific Research [26702034, 15H03111, 15K07416] Funding Source: KAKEN
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A biomimetic synthesis of naturally occurring lactams rubrobramide, flavipucine, and isoflavipucine is described. The key step is a regioselective Darzens reaction between isobutyl glyoxal and an alpha-bromo-beta-ketoamide. The construction of the core tricyclic ring system of rubrobramide was achieved by a cascade reaction in a single step from an a, beta-epoxy-gamma-lactam. Furthermore, the absolute configuration of naturally occurring (+)-rubrobramide was determined by vibrational circular dichroism. (+/-)-Flavipucine and (+/-)-isoflavipucine were synthesized from an epoxyimide, which was prepared by reaction of isobutyl glyoxal with a protected a-bromo-b-ketoamide. Deprotection of the epoxyimide and formation of the pyridone ring gave (+/-)-flavipucine, which was converted into (+/-)-isoflavipucine by thermal isomerization.
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