Synthesis of the heptacyclic indole alkaloid (.+-.)-kopsine and related studies
β Scribed by Magnus, Philip; Katoh, Tadashi; Matthews, Ian R.; Huffman, John C.
- Book ID
- 120938410
- Publisher
- American Chemical Society
- Year
- 1989
- Tongue
- English
- Weight
- 602 KB
- Volume
- 111
- Category
- Article
- ISSN
- 0002-7863
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## Abstract An improved method for obtaining optically pure (__S__)β(lβ__p__βmenthenβ8βyl)amine (**12**) has led to expedient syntheses of two hypothetical biogenetic intermediates on the way to aistoteline (**7**), namely (__S__)β(__N__)β(lβ__p__βmenthenβ8βyl)β2β(3βindolyl)ethylamine (**3**) and (
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 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