630103-80-9Relevant articles and documents
Structure elucidation of a pungent compound in black cardamom: Amomum tsao-ko Crevost et Lemarie (Zingiberaceae)
Starkenmann, Christian,Mayenzet, Fabienne,Brauchli, Robert,Wunsche, Laurent,Vial, Christian
, p. 10902 - 10907 (2007)
Natural plant extracts containing taste modifier compounds will gain more commercial interest in the future. Black cardamom, Amomum tsao-ko Crevost et Lemarie, used as a spice in Asia, produces a nice refreshing effect in the mouth. Therefore, an ethyl acetate extract was prepared, and constituents were separated by liquid chromatography. Guided by the tasting of each fraction (LC tasting), a new pungent compound was discovered, (±)-trans-2,3,3a,7a- tetrahydro-1H-indene-4-carbaldehyde. To confirm this new structure, a synthesis was performed starting from cyclopentene-1-carbaldehyde. The Wittig conditions were determined to control the stereochemistry of the ring fusion to prepare (±)-trans-(2,3,3a,7a-tetrahydro-1H-inden-4-yl) methanol and (±)-cis-(2,3,3a,7a-tetrahydro-1H-inden-4-yl) methanol. After oxidation, (±)-trans-2,3,3a,7a-tetrahydro-1H-indene-4-carbaldehyde and (±)-cis-2,3,3a,7a-tetrahydro-1H-indene-4-carbaldehyde were tasted in water and only the trans-2,3,3a,7a-tetrahydro-1H-indene-4-carbaldehyde, present in black cardamom, produced a trigeminal effect in the mouth.
Useful Enantioselective Bicyclization Reactions Using an N-Protonated Chiral Oxazaborolidine as Catalyst
Zhou, Gang,Hu, Qi-Ying,Corey
, p. 3979 - 3982 (2007/10/03)
(Equation Presented) Nine examples are reported of enantioselective [4 + 2] cycloaddition reactions of achiral, acyclic substrates to form chiral bicyclo[4.3.0]-nonane or bicyclo[4.4.0]decane derivatives.