Assignment of the Absolute Configuration of Concentricolide – Absolute Configuration Determination of Its Bioactive Analogs Using DFT Methods

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 & Co. KGaA, 69451 Weinheim, Germany, 2009)