1032325-86-2Relevant academic research and scientific papers
Total synthesis of (+)-alexine by utilizing a highly stereoselective [3+2] annulation reaction of an TV-tosyl-α-amino aldehyde and a 1,3-bis(silyl)propene
Dressel, Martina,Restorp, Per,Somfai, Peter
experimental part, p. 3072 - 3077 (2009/04/11)
A novel route towards the polyhydroxylated pyrrolizidine alkaloid (+)-alexine has been developed. A key step in this synthesis is a highly stereoselective [3+2] annulation reaction of N-Ts-α-amino aldehyde 7a (Ts=tosyl) and 1,3-bis(silyl)propene 8a for the construction of the polyhydroxylated pyrrolidine subunit of the target molecule. Previous synthetic strategies rely on carbohydrates that require several protecting-group manipulations, there-by making the total number of steps relatively high. The [3+2] annulation strategy compares favorably with carbohydrate-based syntheses and constitutes a highly efficient entry to polyhydroxylated alkaloids.
