ABSOLUTE CONFIGURATION OF THE MERODITERPENOIDS TAONDIOL AND EPITAONDIOL DIACETATES BY VIBRATIONAL CIRCULAR DICHROISM

作者：Munoz Marcelo A^*; Areche Carlos; Rovirosa Juana; San Martin Aurelio; Gordillo Roman Barbara; Joseph Nathan Pedro

来源：Heterocycles, 2012, 85(8): 1961-1973.

DOI：10.3987/COM-12-12514

• Absolute Configuration
• Vibrational Circular Dichroism
• Taondiol Diacetate
• Epitaondiol Diacetate
• Meroditerpenoid

The absolute configuration of alga meroditerpenoids (-)-taondiol diacetate (1b) and (+)-epitaondiol diacetate (2c) are assigned by vibrational circular clichroism (VCD). The spectra of (2S,35,6R,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.

• 出版日期2012-8-1