Asymmetric synthesis of cis- and trans-2,5-disubstituted pyrrolidines from 3-oxo pyrrolidine 2-phosphonates: synthesis of (+)-preussin and analogs

Franklin A Davis; Junyi Zhang; Hui Qiu; Yongzhong Wu

doi:10.1021/ol800255r

Asymmetric synthesis of cis- and trans-2,5-disubstituted pyrrolidines from 3-oxo pyrrolidine 2-phosphonates: synthesis of (+)-preussin and analogs

Org Lett. 2008 Apr 3;10(7):1433-6. doi: 10.1021/ol800255r. Epub 2008 Mar 11.

Authors

Franklin A Davis¹, Junyi Zhang, Hui Qiu, Yongzhong Wu

Affiliation

¹ Department of Chemistry, Temple University, Philadelphia, Pennsylvania 19122, USA. [email protected]

PMID: 18331047
DOI: 10.1021/ol800255r

Abstract

Pyrrolidine enones, derived from 3-oxo pyrrolidine 2-phosphonates and a HWE reaction with aldehydes, on Luche reduction give pyrrolidine allylic alcohols. The alcohols on hydrogenation (Pd/H2) give cis-2,5-disubstituted pyrrolidines and on treatment with TFA-NaBH3CN undergo a hydroxy directed reduction to trans-2,5-disubstituted pyrrolidines.

Publication types

Research Support, N.I.H., Extramural

MeSH terms

Anisomycin / analogs & derivatives*
Anisomycin / chemical synthesis
Anisomycin / chemistry
Catalysis
Organophosphonates / chemistry*
Pyrrolidines / chemical synthesis*
Pyrrolidines / chemistry
Stereoisomerism

Substances

Organophosphonates
Pyrrolidines
preussin
Anisomycin

Abstract

Publication types

MeSH terms

Substances

Grants and funding