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Vilma Masaitis

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Jan 25, 2024, 2:29:21 AM1/25/24
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Compound 2 is structurally similar to compound 1, except that the prenyl moiety is attached to the phenalenone part as a trimethyl dihydrofuran ring (Figure 1) as follows. HMBC correlations (Table 2) allowed connecting the C-15 to C-19 part of the molecule, which is an oxygenated hemiterpene unit. C-17 of this partial structure was attached to C-1 of the aromatic moiety due to heteronuclear long range couplings of H3-18 and H2-19 to C-1. Ring closure to a dihydrofuran ring occurred via the oxygen atom at C-15 to C-14 of the aromatic nucleus. The complete structural identification of 2 was done by extensive spectroscopic data (Table 1 and Table 2). Compound 2 was isolated in this work as an epimeric pure form for the first time (Figure S7), and it was reported before as an epimeric mixture at C-15 under the name dehydroazasirosterol [5]. Therefore, we gave the name conio-azasterol and S-dehydroazasirosterol for compounds 1 and 2, respectively.

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