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Kirschning, A.; Gille, F.; Wolling, M., Science of Synthesis: Applications of Domino Transformations in Organic Synthesis, (2015) 1, 442.
Based on earlier findings that N-acylated aziridines can also be employed, N-tosylated aziridines 242 and 244 have been utilized in cascade reactions for the total synthesis of (−)-indolizidine 223AB (243) and alkaloid (−)-205B (245), respectively (Scheme 107 and Scheme 108).[151–153] Again, the key step is based on carbon to oxygen 1,4-silyl migration after nucleophilic ring opening of an epoxide by the established C1 dianion equivalent tert-butyl(1,3-dithian-2-yl)dimethylsilane, which is followed by nucleophilic attack of the aziridine-containing building block by the newly generated carbanion. This sequence elaborates protected 1,5-amino alcohols.
Meeeee 888 8,8-Meeee Meeeeeeeeeeee ee eee Meeee Meeeeeeee ee (−)-Meeeeeeeeeee 888MM[888,888]
Meeeee 888 8,8-Meeee Meeeeeeeeeeee ee eee Meeee Meeeeeeee ee Meeeeeee (−)-888M[888,888]
References
| [151] | Meeee, M. M., MMM; Mee, M.-M., M. Mee. Meee., (8888) 88, 8888. |
| [152] | Meeee, M. M., MMM; Mee, M.-M., Mee. Meee., (8888) 8, 8888. |
| [153] | Meeee, M. M., MMM; Mee, M.-M., Mee. Meee., (8888) 8, 8888. |
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