Leptosperols A and B (1 and 2), two cinnamoylphloroglucinol–sesquiterpenoid
hybrids featuring unprecedented 1-benzyl-2-(2-phenylethyl) cyclodecane
and 2-benzyl-3-phenylethyl decahydronaphthalene backbones, along with
their biosynthetic precursor (3), were isolated from Leptospermum scoparium. Compounds 1 and 2 represent the first example of phloroglucinol derivatives
biogenetically constructed by a De Mayo reaction. The biomimetic synthesis
of leptosperol B (2) was achieved using the proposed
biosynthetic pathway. In addition, compounds 1 and 2 showed significant anti-inflammatory effects in zebrafish
acute inflammatory models.
A pair of enantiomeric triketone−phloroglucinol hybrids, (+)-and (−)-myrtuspirone A (1), featuring an unprecedented 3-isopropyl-3H-spiro[benzofuran-2,1′-cyclohexane] backbone, were isolated from the leaves of Myrtus communis. The absolute configuration of each enantiomer of 1 was determined by X-ray diffraction and chemical calculations. Furthermore, the gram-scale total syntheses of (±)-1 and (−)-1 were conducted in four steps using a Michael-Niodosuccinimide (NIS)-mediated (3 + 2)-annulation reaction. Both (+)-and (−)-1 exhibited antibacterial activities against Gram-positive bacteria including multidrug-resistant strains.
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