Criteria for the determination of the stereochemistry of steroidal indolizidines
Abstract
E/F-Indolizidine steroids, which represent a structural unit of Solanum alkaloids, have been synthesized and used to evaluate criteria (IR—Bohlmann bands,1a-c —hydrogenbond,2a-e NMR,3a-c mass spectra,4 kinetic studies of quaternization with methyl iodide,5a,b oxidation with mercuric acetate6) for the determination of the stereochemistry of these systems. It was found that the most reliable method is the measurement of the rate constants of quaternization of the bridgehead nitrogen with methyliodide.
Keywords:
stereochemistry / indolizidines / steroidal indolizidinesSource:
Tetrahedron, 1974, 30, 4, 2233-2237Publisher:
- Elsevier
Funding / projects:
- The Research Fund of the Serbian Academy of Sciences and Arts SR Serbia, Yugoslavia
Collections
Institution/Community
IHTMTY - JOUR AU - Kolb, V.M. AU - Stefanović, M. PY - 1974 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/4718 AB - E/F-Indolizidine steroids, which represent a structural unit of Solanum alkaloids, have been synthesized and used to evaluate criteria (IR—Bohlmann bands,1a-c —hydrogenbond,2a-e NMR,3a-c mass spectra,4 kinetic studies of quaternization with methyl iodide,5a,b oxidation with mercuric acetate6) for the determination of the stereochemistry of these systems. It was found that the most reliable method is the measurement of the rate constants of quaternization of the bridgehead nitrogen with methyliodide. PB - Elsevier T2 - Tetrahedron T1 - Criteria for the determination of the stereochemistry of steroidal indolizidines VL - 30 IS - 4 SP - 2233 EP - 2237 DO - 10.1016/S0040-4020(01)97363-6 ER -
@article{ author = "Kolb, V.M. and Stefanović, M.", year = "1974", abstract = "E/F-Indolizidine steroids, which represent a structural unit of Solanum alkaloids, have been synthesized and used to evaluate criteria (IR—Bohlmann bands,1a-c —hydrogenbond,2a-e NMR,3a-c mass spectra,4 kinetic studies of quaternization with methyl iodide,5a,b oxidation with mercuric acetate6) for the determination of the stereochemistry of these systems. It was found that the most reliable method is the measurement of the rate constants of quaternization of the bridgehead nitrogen with methyliodide.", publisher = "Elsevier", journal = "Tetrahedron", title = "Criteria for the determination of the stereochemistry of steroidal indolizidines", volume = "30", number = "4", pages = "2233-2237", doi = "10.1016/S0040-4020(01)97363-6" }
Kolb, V.M.,& Stefanović, M.. (1974). Criteria for the determination of the stereochemistry of steroidal indolizidines. in Tetrahedron Elsevier., 30(4), 2233-2237. https://doi.org/10.1016/S0040-4020(01)97363-6
Kolb V, Stefanović M. Criteria for the determination of the stereochemistry of steroidal indolizidines. in Tetrahedron. 1974;30(4):2233-2237. doi:10.1016/S0040-4020(01)97363-6 .
Kolb, V.M., Stefanović, M., "Criteria for the determination of the stereochemistry of steroidal indolizidines" in Tetrahedron, 30, no. 4 (1974):2233-2237, https://doi.org/10.1016/S0040-4020(01)97363-6 . .