A concise and stereoselective synthesis of hydroxypyrrolidines: rapid synthesis of (+)-preussin.
A convergent and stereoselective synthesis of 2,5-disubstituted 3-hydroxypyrrolidines has been developed that involves reductive annulation of β-iminochlorohydrins, which are readily available from β-ketochlorohydrins, and provides rapid access to a variety of 2,5-syn-pyrrolidines. Application of this process to the concise (three-step) synthesis of the fungal metabolite (+)-preussin and analogues of this substance is reported.
Draper
Jason A
JA
Department of Chemistry, Simon Fraser University, Burnaby, British Columbia V5A 1S6, Canada.
Britton
Robert
R
D000841:Anisomycin / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D015394:Molecular Structure; D013237:Stereoisomerism; D013997:Time Factors
C058280:preussin; D000841:Anisomycin