Untitled

A Straightforward Hetero‐Diels–Alder Approach to (2‐ambo,4′R,8′R)‐α/β/γ/δ‐4‐Thiatocopherol

“…Our initial strategy, foresaw the transformation of 7 into (6R,10R)-6,10,14-trimethylpentadeca-2-one (10), known as phytone, [15] followed by the one-pot conversion of the latter into diene 8 as recently reported in the literature. [16] The synthesis of enantiopure ketone 10 was easily achieved, in two steps and very good yield, by OsO 4 /NMO mediated dihydroxylation followed by a Pb(OAc) 4 oxidation (Scheme 4).…”

New possibilities in a synthesis of (2R,4'R,8'R)-α-tocopherol (natural vitamin E).

“…The specific activity of lipase from Candida cylindracea (CCL, Fluka) was 3.85 ед·мг 1.1º (c 1.78, CHCl 3 )) was synthesized according to the our method, described earlier. 12 Methods of synthesis, spectral data (HNMR, IR, elemental analysis) and specific angles of rotation of compounds 2-7 described in our manuscripts. 54 mmol) in dichloromethane (2 ml) at a temperature of -70˚C was added oxalylcholoride (0.11 ml, 1.32 mmol) and stirred for 0.5 h. A solution of (S)-9 (0.05 g, 0.16 mmol) in dichloromethane (2 ml) was added and stirred for 1 h at -70˚C.…”

Synthesis of triterpene acids conjugates with α-tocopherol synthetic analogs

“…The debenzylation of compounds XIIa and XIIb cleanly proceeded by hydrogenation in the presence of Pd/C catalyst in ethyl ether ended to the formation of adducts XIIc and XIId in a quantitative yield, yet we failed to perform these reactions in ethanol evidently due to the low solubility of compounds XIIa and XIIb. In order to prepare conjugate XVII naphthotocopherol (XIII) synthesized directly before the reaction by procedure [25] was acylated with N-(benzyloxycarbonyl) glycine (CBz-Gly) in the presence of DCC and catalytic amount of DMAP. The reaction gave O-acyl derivative of naphthotocopherol XIV in a high yield.…”