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Substituent-directed oxidation: Transannular oxidative cyclization of cycloalkenols to β-keto cyclic ethers.

✍ Scribed by Matthew F. Schlecht; Ho-jin Kim

Publisher: Elsevier Science
Year: 1986
Tongue: French
Weight: 221 KB
Volume: 27
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)85089-3

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✦ Synopsis

Treatment of the tertiary cyclooctenolz with lead tetraacetate or with chromium(V1) reagents results in transannular oxidative cyclization to 8-functionalized bicyclic ethers, and the selectivity between the oxabicyclo[3.3.l]nonane and the oxabicyclo[4.2.l]nonane skeleton depends on the nature of the oxidizing agent.

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