The stereochemistry of C15 in annotinine
โ Scribed by Tse-Lok Ho
- Publisher
- Elsevier Science
- Year
- 1969
- Tongue
- French
- Weight
- 102 KB
- Volume
- 10
- Category
- Article
- ISSN
- 0040-4039
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โฆ Synopsis
The structure of the Lycopodium alkaloid annotinine (I) and the configuration of all its asymmetric centers except C l5 was deduced by :iiesner and his coworkers (l), and was later fully corroborated by an X-ray diffraction analysis of the derived bnnnohydrin Recently, an elegant first total
๐ SIMILAR VOLUMES
The Igaopodium alkaloid annotinine I (1) was aonverted by MacLean and prime (2) in a simple three-step sequenae to the lactam II. We nnw wish to report the tgtal synthesis of this aompound.
The electroreduction mechanism of +haIogen derivatives of organic compounds in proton donating solvents was investigated on the exampie of optically active 2-phenyl-2-chloropropionic acid. It was shcwn that the electroreduction occurs with inversion of configuration according to the SN2 mechanism.
By comparison of the CD-spectra of synthetic material with that of stegobinone it is established that stegobinone has the 2S,3R-configuration. The stereochemistry at C-7 remains unknown at present.