Asymmetric Total Synthesis of (+)-2-epi-Deoxoprosopinine
- 31 December 2000
- journal article
- special topic
- Published by Georg Thieme Verlag KG in Synthesis
- Vol. 2000 (14) , 2099-2105
- https://doi.org/10.1055/s-2000-8733
Abstract
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.Keywords
This publication has 0 references indexed in Scilit: