Rhodomentosones A and B (1 and 2), two
pairs of novel enantiomeric phloroglucinol trimers featuring a unique
6/5/5/6/5/5/6-fused ring system were isolated from Rhodomyrtus
tomentosa. Their structures with absolute configurations
were elucidated by NMR spectroscopy, X-ray crystallography, and ECD
calculation. The bioinspired syntheses of 1 and 2 were achieved in six steps featuring an organocatalytic
asymmetric dehydroxylation/Michael addition/Kornblum–DeLaMare
rearrangement/ketalization cascade reaction. Compounds 1 and 2 exhibited promising antiviral activities against
respiratory syncytial virus (RSV).
Rhodotomentones A and B (1 and 2), two unusual caryophyllene-derived meroterpenoids (CDMTs) featuring a rare 6/6/9/4/6/6 hexacyclic ring system, along with their biogenetically-related CDMTs 7 and 12–15, were isolated from Rhodomyrtus tomentosa.
Inspired by a previously reported
biomimetic synthesis study, four
new naturally occurring phloroglucinol trimers 1–4 with unusual 6/5/5/6/6/6-fused hexacyclic ring systems, along with
two known analogues (5 and 6) and two known
biogenetically related dimers (10 and 11), were isolated from Rhodomyrtus tomentosa. Their structures and absolute configurations were unambiguously
elucidated by spectroscopic analysis, X-ray diffraction, and electronic
circular dichroism calculation. By mimicking two potentially alternative
biosynthetic pathways, the first asymmetric syntheses of 1–4 and the racemic syntheses of 5 and 6 were
achieved in only five to six steps without the need for protecting
groups. Furthermore, phloroglucinol dimers 10 and 11 exhibited significant in vitro antiviral activity against
the respiratory syncytial virus.
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