Organocatalytic asymmetric total synthesis of (R)-rolipram and formal synthesis of (3S,4R)-paroxetine

Peter S Hynes; Paul A Stupple; Darren J Dixon

doi:10.1021/ol800108u

Organocatalytic asymmetric total synthesis of (R)-rolipram and formal synthesis of (3S,4R)-paroxetine

Org Lett. 2008 Apr 3;10(7):1389-91. doi: 10.1021/ol800108u. Epub 2008 Mar 7.

Authors

Peter S Hynes¹, Paul A Stupple, Darren J Dixon

Affiliation

¹ School of Chemistry, The University of Manchester, Oxford Road, Manchester, M13 9PL, United Kingdom.

PMID: 18324820
DOI: 10.1021/ol800108u

Abstract

An efficient enantioselective total synthesis of (R)-rolipram and an efficient enantioselective formal synthesis of (3S,4R)-paroxetine has been achieved using the highly enantioselective Michael addition of malonate nucleophiles as key steps in both cases.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Catalysis
Malonates / chemistry
Molecular Structure
Paroxetine / chemical synthesis*
Paroxetine / chemistry
Rolipram / chemical synthesis*
Rolipram / chemistry
Stereoisomerism

Substances

Malonates
Paroxetine
malonic acid
Rolipram