Synthesis of 2-(dimethylallyl)-N-hydroxytryptophans from indole
β Scribed by Ralf Plate; Harry C.J Ottenheijm
- Publisher
- Elsevier Science
- Year
- 1986
- Tongue
- French
- Weight
- 234 KB
- Volume
- 27
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
A mild and general method for the synthesis of dimethylallyl tryptophan derivatives 11 and 12 is described. Reaction of the 3-(r,X-dimethyl-allyl) indoles i'a or 7b with the nitroso olefin 8 yields the cycloadducts 9a (93%) and 9b (87%), respectively. Subsequent treatment of 9a with trifluoroacetic
π SIMILAR VOLUMES
## Abstract For Abstract see ChemInform Abstract in Full Text.
2S,3R)-N-(1%,1%-Dimethyl-2%-propenyl)-3-hydroxytryptophan, a key amino acid of the anti-inflammatory cyclic peptide, cyclomarin C, has been synthesized stereoselectively, with full protection, from L-tryptophan for the first time.
A practical synthesis of pyrrolo [3,2-e]indole (1) is described. Different hydrogenation conditions of the indol-4-ylacetonitrile (3) afforded either l-BOM-pyrrolo[3,2-e]indole (4, 42% from 5nitroindole) or I-hydroxymethylpyrrolo[3,2-e]indole (5, 46% from 5-nitroindole). Removal of the benzyl group