767272-87-7Relevant academic research and scientific papers
Asymmetric routes towards polyfunctionalized pyrrolidines: A short diastereoselective synthesis of polyhydroxylated pyrrolidines and an indolizidine
Dudot, Bruno,Micouin, Laurent,Baussanne, Isabelle,Royer, Jacques
, p. 688 - 694 (2007/10/03)
Various (2S,3S,4R)-2-[(1R)-1-hydroxyalkyl]pyrrolidine-3,4-diols (11) have been prepared in 8 steps and 13-20% overall yield starting from (R)-(- )-phenylglycinol. This concise approach is based on the condensation of a chiral silyloxypyrrole with aldehydes which gave the (R,R)-aldol compounds in good yields and high diastereoselectivities. The cis-hydroxylation followed by reduction and deprotection gave the desired trihydroxylated pyrrolidines. The same strategy has been successively applied to a formal synthesis of 8a- epi-swainsonine.
