Claisen rearrangement in indole alkaloid synthesis. Total synthesis of (+-)-tabersonine
โ Scribed by Ziegler, Frederick E.; Bennett, Gregory B.
- Book ID
- 120249309
- Publisher
- American Chemical Society
- Year
- 1973
- Tongue
- English
- Weight
- 1021 KB
- Volume
- 95
- Category
- Article
- ISSN
- 0002-7863
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๐ SIMILAR VOLUMES
The tetrahedrane framework with R=tBu and the octabisvalene framework with R = CH3 presumably form because of steric reasons. Whereas the hydrocarbon 2 is highly strained, the arrangement in 1 is largely strain-free, based on the intermolecular contact distances. With other residues R the occurrenc
We wish to report a facile thermal rearrangement of an N-aryl propynylamine oxide to an indole. The present study, to our knowledge, is the first report of such a rearrangement. Compound 1 (89.5%; m.p. 76-77)\* was prepared by the condensation of l-(4-chlorophenoxy)-4chloro-2-butyne3 with two moles