Abstract
We report the first total synthesis of four possible absolute configurations and four other regional isomers of a naturally occurring alkaloid crotonine, which was isolated from Croton tiglium L. (Euphoriaceae) without elucidation of its absolute configuration. The concise five-step route with a chirally poor and regioselective strategy starting from monosaccharides was established, and the absolute structure of the natural crotonine was determined by comparison of the NMR spectra and optical rotations of the synthetic products. Electronic Supplementary MaterialSupplementary material is available for this article at 10.1007/s13659-013-0080-1 and is accessible for authorized users.
Highlights
Pyrazines are important components of processed foods and are associated with the generation of flavor and color, such as those of fermented cacao, cheese and wines.[1]
The Maillard reaction of amino acids with reducing sugars has become the primary process for generating these pyrazine derivatives in food processing.[2]
To determine the absolute structure of natural crotonine, a concise saccharide-based fivestep route was developed for the synthesis of all possible chiral isomers
Summary
Pyrazines are important components of processed foods and are associated with the generation of flavor and color, such as those of fermented cacao, cheese and wines.[1]. (Euphoriaceae) without determination of the absolute configuration. The analgesic properties were obvious compared to those of morphine.[7] To determine the absolute structure of natural crotonine, a concise saccharide-based fivestep route was developed for the synthesis of all possible chiral isomers. The condensation reaction of diamines with diols,[8] hydroxyketones[9] and diketones[10] under catalysis by a transitional metal or base are the main reaction types reported in the literature. Inexpensive monosaccharides were adopted as the starting material and chirality source for the preparation of α-dicarbonyl intermediates.[11] Pyrazine condensation of the diamine and 3-deoxy-aldos-2uloses intermediates, which is the key step in the reaction sequence, was catalyzed by potassium hydroxide, and other
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