Subscribe to RSS
Asymmetric Total Synthesis of (+)-2-epi-Deoxoprosopinine
31 December 2000 (online)
The asymmetric synthesis of (+)-2-epi-deoxoprosopinine [(S,S,R)-5] in eleven steps and with excellent diastereomeric and enantiomeric purity (de, ee ≥96%) is described. As key steps, the 1,2-addition of a dodecyl nucleophile to an aldehyde-SAMP hydrazone and the α-alkylation of 2,2-dimethyl-1,3-dioxan-5-one SAMP hydrazone are employed to generate two of the three stereogenic centers. Creation of the third stereogenic center was achieved in a domino deprotection/cyclisation/reduction sequence.
asymmetric synthesis - deoxoprosopinine - SAMP/RAMP hydrazone method - natural products - piperidine alkaloids