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Paper | Regular issue | Vol 85, No. 8, 2012, pp.1961-1973
Published online, 27th June, 2012
DOI: 10.3987/COM-12-12514
Absolute Configuration of the Meroditerpenoids Taondiol and Epitaondiol Diacetates by Vibrational Circular Dichroism

Marcelo A. Muñoz, Carlos Areche, Juana Rovirosa, Aurelio San Martín, Bárbara Gordillo-Román, and Pedro Joseph-Nathan*

*Departamento de Química, Centro de Investigación y de Estudios Avanzados del Instituto Politécnico Nacional, A.P. 14-740, Avenida IPN 2508, Esquina Ticoman, C.P. 07000 México, D.F., Mexico

Abstract

The absolute configuration of alga meroditerpenoids ()-taondiol diacetate (1b) and (+)-epitaondiol diacetate (2c) are assigned by vibrational circular dichroism (VCD). The spectra of (2S,3S,6R,7R,10R,11R,14S)-1b and (2S,3S,6S,7S,10R,11R,14S)-2c enantiomers, calculated at the B3LYP/DGDZVP and at the B3LYP/DGDZVP2 levels of theory, respectively, matched confidently with the experimental ones. The numerical approach using neighborhood similarity indexes in the CompareVOA algorithm software supports the assignments with 100% confidence. The X-ray diffraction structures of 1b and 2c were determined to verify their relative stereochemistry and the crystal stereostructure of the meroditerpenoid stypotriol triacetate (5) is also reported.