Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 76, Issue 6, Pages 1852-1873Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo2000308
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Funding
- National Institutes of Health [GM 28273]
- Merck Research Laboratories
- Boehringer Ingelheim Pharmaceuticals
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A two-stage tandem strategy for the synthesis of benzofused nitrogen heterocycles is described that is particularly useful for the construction of systems with a high level of substitution on the benzenoid ring. The first stage in the strategy involves a benzannulation based on the reaction of cyclobutenones with ynamides. This cascade process proceeds via a sequence of four pericyclic reactions and furnishes a multiply substituted aniline derivative which can bear a variety of functionalized substituents at the position ortho to the nitrogen. In the second stage of the tandem strategy, ring-closing metathesis generates the nitrogen heterocyclic ring. This two-step sequence provides efficient access to highly substituted dihydroquinolines, benzazepines, benzazocines, and related benzofused nitrogen heterocyclic systems. The application of this chemistry in a concise formal total synthesis of the anticancer agents (+)-FR900482 and (+)-FR66979 is described.
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