Nudicaulins, yellow flower pigments of Papaver nudicaule: revised constitution and assignment of absolute configuration

Evangelos C Tatsis; Anu Schaumlöffel; Anne C Warskulat; Georges Massiot; Bernd Schneider; Gerhard Bringmann

doi:10.1021/ol303211w

Nudicaulins, yellow flower pigments of Papaver nudicaule: revised constitution and assignment of absolute configuration

Org Lett. 2013 Jan 4;15(1):156-9. doi: 10.1021/ol303211w. Epub 2012 Dec 18.

Authors

Evangelos C Tatsis¹, Anu Schaumlöffel, Anne C Warskulat, Georges Massiot, Bernd Schneider, Gerhard Bringmann

Affiliation

¹ Max Planck Institute for Chemical Ecology, Hans-Knöll-Strasse 8, Beutenberg Campus, 07745 Jena, Germany.

PMID: 23249326
DOI: 10.1021/ol303211w

Abstract

The constitution of the aglycon of nudicaulin has been revised to be a pentacyclic indole alkaloid. The relative and absolute configurations of the two diastereomers, nudicaulins I (3a) and II (3b), have been assigned by NMR, conformational analyses, and interpretation of the experimental ECD spectra by quantum-chemical calculations.

Publication types

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

MeSH terms

Flowers / chemistry
Indole Alkaloids / chemistry*
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Papaver / chemistry*
Pigments, Biological / chemistry*
Stereoisomerism

Substances

Indole Alkaloids
Pigments, Biological