Bilinguals and religiosity

Prenylated Acetophloroglucinol Dimers from Acronychia trifoliolata: Structure Elucidation and Total Synthesis

“…4, 203.9), two pairs of olefinic carbons (δ C 132.0, 131.9, 122.5, 123.0), 12 aromatic carbons (δ C 161.6, 161.4, 161.3, 161.1, 160.4, 158.7, 117.9, 116.3, 115.4, 110.2, 111.0, 108.7), and an oxymethine (δ C 79.1), which suggested the presence of two phenyl rings. These signals were very similar to those of sideroxylonal C, isolated from Eucalyptus albens 15 and E. melliodora, 16 except for the two pairs of prenyl groups and two acetyl groups present instead of four formyl groups as well as the two methoxy groups replacing two hydroxy groups. Furthermore, compound 1 showed a protonated molecular ion peak at m/z 637.3744 in the HRFABMS, corresponding to the molecular formula C 38 H 53 O 8 , which suggested that this compound is a dimeric derivative of 1- [2,4-dihydroxy-6-methoxy-3,5-bis(3-methyl-2-buten-1-yl)phenyl]ethanone, previously isolated from the same extract.…”

“…In addition, the isopropyl and isobutyl groups were also trans oriented based on NOESY correlations between H-2′, H-2⁗, and the OH at C-4‴. The assigned relative configuration was supported by a comparison of the H-1′, H-1⁗, and H-2⁗ coupling constants with those of the related phloroglucinol dimers, sideroxylonals A, B, and C. [15][16][17] It should be noted that sideroxylonals A, B, and C [15][16][17] as well as loxophlebal A, 18 four related phloroglucinol dimers with a 4-isobutyl-3-isopropyltetrahydro-2H-pyran unit, were isolated only from the genus Eucalyptus [15][16][17][18][19][20][21] in the family Myrtaceae. They were all racemic with the same planar structure derived from formylated phloroglucinols.…”