Chirality in diarylether heptanoids: synthesis of myricatomentogenin, jugcathanin, and congeners.
The syntheses of myricatomentogenin, jugcathanin, galeon, pterocarine, and acerogenin L are reported. Synthetic material was used to measure their optical activities and free energy of activation for racemization. The natural enantiomers of myricatomentogenin, jugcathanin, galeon, and pterocarine were determined to have the same pR absolute stereochemistry. Acerogenins L and C are achiral compounds.
Department of Chemistry, Oregon State University, 153 Gilbert Hall, Corvallis, Oregon 97331, USA.
M Quamar
MQ
Salih
Christopher M
CM
Beaudry
D036381:Diarylheptanoids / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D013237:Stereoisomerism; D000097566:Cyclophanes
D036381:Diarylheptanoids; C509355:acerogenin L; D000097566:Cyclophanes; C576599:jugcathanin; C576598:myricatomentogenin