Diastereoselective multicomponent reaction in water: synthesis of 2-azapyrrolizidine alkaloid analogues

Balakrishnan Rajarathinam; Gnanasambandam Vasuki

doi:10.1021/ol302355w

Diastereoselective multicomponent reaction in water: synthesis of 2-azapyrrolizidine alkaloid analogues

Org Lett. 2012 Oct 19;14(20):5204-6. doi: 10.1021/ol302355w. Epub 2012 Oct 1.

Authors

Balakrishnan Rajarathinam¹, Gnanasambandam Vasuki

Affiliation

¹ Department of Chemistry, Pondicherry University, Puducherry 605 014, India.

PMID: 23025468
DOI: 10.1021/ol302355w

Abstract

Synthesis of the 2-aza analogues of the pyrrolizidine alkaloid motif with two contiguous stereocenters has been achieved with high regio-, chemo-, and diastereoselectivity by an innovative multicomponent reaction in water. This elegant tactic has integrated the principles of privileged substructure-based Diversity Oriented Synthesis (pDOS) and Biology Oriented Synthesis (BIOS) to access a biologically relevant scaffold.

Publication types

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

MeSH terms

Aza Compounds / chemical synthesis*
Models, Molecular
Molecular Structure
Pyrrolizidine Alkaloids / chemical synthesis*
Stereoisomerism
Water / chemistry

Substances

Aza Compounds
Pyrrolizidine Alkaloids
Water