491-05-4Relevant articles and documents
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Horiuchi
, p. 314,316 (1935)
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Protecting group free enantiospecific total syntheses of structurally diverse natural products of the tetrahydrocannabinoid family
Dethe, Dattatraya H.,Erande, Rohan D.,Mahapatra, Samarpita,Das, Saikat,Kumar B., Vijay
supporting information, p. 2871 - 2873 (2015/03/03)
A simple, highly diastereoselective, Lewis acid catalyzed Friedel-Crafts coupling of a cyclic allylic alcohol with resorcinol derivatives has been developed. The method was applied for the enantiospecific total syntheses of structurally diverse natural products such as machaeriol-D, Δ8-THC, Δ9-THC, epi-perrottetinene and their analogues. Synthesis of both natural products and their enantiomers has been achieved with high atom economy, in a protecting group free manner and in less than 6 steps, the longest linear sequence, in a very good overall yield starting from R-(+) and S-(-)-limonene.
3-Alkyl-p-menthan-3-ol derivatives: synthesis and evaluation of their physiological cooling activity
Fuganti, Claudio,Joulain, Daniel,Maggioni, Francesco,Malpezzi, Luciana,Serra, Stefano,Vecchione, Andrea
body text, p. 2425 - 2437 (2009/04/06)
Different 3-alkyl-p-methan-3-ol derivatives provide a strong physiological cooling effect with potential application as food and cosmetic additives. In order to investigate the influence of the chemical structure on the cooling sensation, the stereoselective syntheses of 29 different 3-alkyl-p-methan-3-ol derivatives were accomplished. All the compounds obtained are odorless and were evaluated by taste, considering two sensations: a cooling effect and bitterness. The results of this structure-activity relationship study highlight that compounds with a (1R,4S)-configuration are the isomers with the more intense cooling effect and lower bitterness. In addition, the structure of the 3-alkyl chain affected the latter properties. Increasing the chain length over two carbon atoms does not change the cooling power, but enhances the bitterness with the additional feature that the branched isomers are considerably more bitter than the linear ones. Overall, the 3-alkyl-p-menthan-3-ol isomers with the best quality in terms of high cooling power and low bitterness are (1R,4S)-3-(hydroxymethyl)-p-menthan-3-ol diastereoisomers (-)-38 and (-)-42.