✦ LIBER ✦
Preparation of functionalized hydroindol-3-ols via tandem aza-Cope rearrangement-mannich cyclizations. Formal total synthesis of (+)-6a-epipretazettine and related alkaloids
✍ Scribed by Larry E. Overman; Hanno Wild
- Publisher
- Elsevier Science
- Year
- 1989
- Tongue
- French
- Weight
- 248 KB
- Volume
- 30
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
Key steps in this approach to umaryllidaceae alkaloids containing oxidation at the R-position of the pyrroline ring are (a) copper(H)-promoted rearrangement of aminocyclopentanol 11 to afford the 3-silylhydroindole 12, and (b) oxidation of 12 by the general procedures of Kumada and Fleming to give the cis-3a-aryl-3-hydroxyhexahydroindolone 13 in 71% overall yield from