Assignment of the Absolute Configuration of <i>Concentricolide</i> – Absolute Configuration Determination of Its Bioactive Analogs Using DFT Methods

Abstract

Abstract The configuration of concentricolide was assigned as ( S ). The configuration of its three analogs, which have anti‐HIV‐1 activity, were predicted by optical rotation values obtained by the B3LYP/aug‐cc‐pVDZ//B3LYP/6‐31+G(d) and B3LYP/aug‐cc‐pVDZ//MP2/6‐311+G(d) methods. The two methods predict very close optical rotation magnitudes for all three chiral analogs of concentricolide . The two methods were applied in optical rotation predictions for seven other concentricolide analogs. Circular dichroism calculations were performed for four of the seven analogs at the B3LYP/aug‐cc‐pVDZ level.(© Wiley‐VCH Verlag GmbH &amp; Co. KGaA, 69451 Weinheim, Germany, 2009)