Studies on the Synthesis of Strychnos Indole Alkaloids. Synthesis of (.+-.)-Dehydrotubifoline
β Scribed by Bonjoch, Josep; Sole, Daniel; Bosch, Joan
- Book ID
- 111858625
- Publisher
- American Chemical Society
- Year
- 1995
- Tongue
- English
- Weight
- 256 KB
- Volume
- 117
- Category
- Article
- ISSN
- 0002-7863
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π SIMILAR VOLUMES
Tetracycles 3b-d, having the ABCD ring substructure of Strychnos alkaIoids and a &(formvhnethvl) substituent mokcted as an oxime or hvdraxone derivative. have been p&&d-by nu&phiIic addition of the enolate of indok.a&tic ester 1 to pyridinium salts 2b-d followed by acid cyclization. The same one-pot
The addition of the enolate of methyl 1-methyl-2-indoleacetate 1 and lithium 2-(lithiomethyl)indole-1-carboxylate 5 to pyridines and N-alkylpyridinium salts bearing a chiral auxiliary at the 3-position (tolylsulfinyl, acyl iron complexes, bornane-10,2sultam), with subsequent acid cyclization of the
The total synthesis of3 the %z&no~ indole alkaloid tubifoline and detailed H-and C-NMR data of thisalkaloid are reported. ## Tubifoline is a pentacyclic Stigchao~ indole alkaloid, 1 having the Strychnan skel-eta1 type, whose isolation and structural elucidation were reported by Schmid in 1964. 2