Absolute Configuration of Clemateol

ADEMIR F.MOREL; UBIRATAN F. DA SILVA; ENRIQUE L. LARGHI; IONARA I. DALCOL; MARCELO PEDROSO; JACKSON A. L. C. RESENDE; MATEUS L. STIVANIN; MARCO A. MOSTARDEIRO; ROBERT A. BURROW; ADRIANA Z. GEHN

JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY

SOC BRASILEIRA QUIMICA

Lugar: San Pablo; Año: 2018 vol. 29 p. 881 - 887

0103-5053

The present study reports the determination of absolute stereochemistry of clemateol (1) - an irregular monoterpene containing an epoxy group - which was isolated as the main component from the essential oil of Calea clematidea (Asteraceae). Its absolute stereochemistry was unambiguously established on the basis of detailed NMR spectroscopic evidence (3JH-H analysis, derivatization as Mosher´s esters and NOESY) and also by resonance scattering effects in the single crystal X-ray diffraction resolution of its (R)-mandelic acid ester derivative.