Revision of the absolute configuration of plumericin and isoplumericin from Plumeria rubra

Abstract

The absolute configurations of plumericin (1) and isoplumericin (2), isolated from Plumeria rubra, were reassigned based on a combination of X-ray crystal-structure determination and quantum-mechanical calculations of their circular dichroism (CD) spectra. The experimental CD spectra showed an excellent match with those calculated for the (1S,5R,8R,9R,10R) absolute configuration (corresponding to ent-1 and ent-2, resp.), opposite to that generally accepted and published in the literature. Since the (false) plumericin configuration has been often used to derive the absolute configuration of related iridoids by chemical correlation, their absolute configurations also have to be reconsidered. © 2005 Verlag Helvetica Chimica Acta AG, Zürich.