Synthesis of naturally occurring cinnamyl cinnamates

Abstract

A convenient, high yield and general method is described for the synthesis of cinnamyl cinnamates (1a-f, 2a-c and 2e) from benzaldehydes (7a-f). The aldehydes (7a-f) on reaction with phosphorane (6) provide the (E,E)-cinnamyl cinnamates (1a-f) in high yields together with the (E,Z)-esters (2a-c and 2e) in low yields in the same reaction.

Study on the Constituents of Mexican Propolis and Their Cytotoxic Activity against PANC-1 Human Pancreatic Cancer Cells

“…Known compounds isolated in this study were (E)-cinnamyl benzoate (4), 23 benzyl (E)-cinnamate (5), 24 (E)-cinnamyl (E)cinnamate (6), 25 (2S)-pinostrobin (7), 26 tectochrysin (8), 27 (2R,3R)alpinone-3-acetate (9), 28 izalpinin (10), 29 benzyl (E)-3,4-dimethoxycinnamate (11), 30 (E)-cinnamyl (E)-3,4-dimethoxycinnamate (12), 31 3,3-dimethylallyl (E)-ferulate ( 13), 32 isopent-3-enyl (E)ferulate ( 14), 32 benzyl (E)-ferulate (15), 33 (E)-cinnamyl (E)isoferulate (16), 31 (E)-cinnamic acid (17), 34 (E,E)-cinnamylideneacetic acid (18), 34 benzoic acid (19), 35 (2R,3R)-alpinone (20), 28,36 galangin (21), 37 (2S)-pinocembrin ( 22), 38 benzyl (E)-p-coumarate (23), 33 (2R,3R)-pinobanksin 3-acetate (24), 39 (2R,3R)-pinobanksin 3-propanoate (25), 21 (2R,3R)-pinobanksin 3-isobutyrate (26), 21 (2R,3R)-pinobanksin 3-(2-methyl)-butyrate (27), 12,21 chrysin (28), 22 vanillin (29), 40 (2R,3R)-3,7-dihydroxy-5-methoxyflavanone (30), 41 (E)-3,4-dimethoxycinnamic acid (31), 30 (E)-ferulic acid (32), 42 (E)cinnamyl (E)-p-coumarate (33), 31 (2R,3S)-8-[4-phenylprop-2-en-1-one]-4′,7-dihydroxy-3′,5-dimethoxyflavan-3-ol (34), 43 2-acetyl-1,3-di-(E)-feruloylglycerol (35), 44 2-acetyl-1-(E)-p-coumaroyl-3-(E)-feruloylglycerol (36), 14 2-acetyl-1,3-di-(E)-p-coumaroylglycerol (37), 14 2-acetyl-3-(E)-caffeoyl-1-(E)-p-coumaroylglycerol (38), …”

Nucleophilic Iron Catalysis in Transesterifications: Scope and Limitations

“…To circumvent a loss of material due to volatility of the resulting products we employed p -chloro aryl cinnamate 27 as activating ester in this investigation (Table ) …”

Synthesis of Complex Allylic Esters via C−H Oxidation vs C−C Bond Formation

“…The expansive scope and streamlining potential of this methodology is represented in the construction of known allylic ester intermediates (Table ). Oxidative coupling of unsaturated aryl acids and α-bromo-carboxylic acids with allyl arenes provides a direct and modular route to compounds 1 and 2 (entries 1−5), some of which have been shown to exhibit antibacterial and antifungal activities (entry 1). It is notable that 1.5 equiv of acid can be used with only a moderate reduction in isolated yield (entry 2).…”