Lateral lithiation in terpenes: synthesis of (+)-ferruginol and (+)-sugiol

Cytotoxic and apoptogenic properties of three isolated diterpenoids from Salvia chorassanica through bioassay-guided fractionation

“…Then the sub-fractions were repeatedly subjected to reversed-phase semi-preparative HPLC. This yielded 3.0, 10.3 and 5.0 mg of taxodione (Rodrigues, 2003), ferruginol (Marcos et al, 2010), and 6-hydroxysalvinolone (Rodrigues, 2003) respectively. The structure of these compounds was determined using 1 H NMR and 13 C NMR methods (Table 1).…”

Research into the oxidation of abietic acid–derived enone with atmospheric oxygen

“…The organic layer was dried over Na 2 SO 4 and evaporated to dryness. The residue was chromatographed on silica gel (1% ethyl acetate in hexane) yielding 10.16 g of the methyl abietate 2 (70.75%) as a colorless oil with spectroscopic data consistent with the literature . 1 H NMR (500 MHz, CDCl 3 ): δ 5.77 (s, 1H), 5.37‐5.34 (m, 1H), 3.63 (s, 3H), 2.22 (septet, J = 6.8 Hz, 1H), 2.11‐2.01 (m, 4H), 1.97‐1.92 (m, 1H), 1.90‐1.85 (m, 1H), 1.84‐1.68 (m, 3H), 1.64‐1.53 (m, 3H), 1.25 (, 3H), 1.25‐1.10 (m, 2H), 1.01 (d, J = 6.8 Hz, 3H), 1.00 (d, J = 6.8 Hz, 3H), 0.82 (s, 3H).…”

“…The residue was chromatographed on silica gel (1% ethyl acetate in hexane) yielding 10.16 g of the methyl abietate 2 (70.75%) as a colorless oil with spectroscopic data consistent with the literature. 8…”

“…remarkable biological activities with proven or potential pharmacological applications. [7][8][9][10] Abietic acid has also been successfully used as a substrate in the synthesis of a structurally complex and diverse collection of small molecules, including other terpenes, utilized in a variety of biological screens. 3,11,12 Therefore, the use of abietic acid in organic synthesis is advantageous despite the ease with which it undergoes self-oxidation under aerial exposure.…”

Lateral lithiation and substitution of N'-(2-methylphenyl)-N,N-dimethylurea

“…1,2 Various heteroatom-based stabilizing groups, located at an ortho-position, have been used successfully for lateral lithiations. [3][4][5][6][7][8][9][10][11][12][13][14][15][16] In the course of our own studies of lithiation reactions 17 we have synthesized various substituted aromatics and heterocycles via efficient lateral lithiation procedures. [18][19][20][21][22] For example, we have successfully laterally lithiated and substituted N'- (2-methylbenzyl)-N,N-dimethylurea (1) with tert-butyllithium (t-BuLi; 2.2 equiv.)…”