Synthesis and Characterization of Enantiomerically Pure Menthylamines and Their Isocyanates

Abstract

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Structural and in Vitro Functional Characterization of a Menthyl TRPM8 Antagonist Indicates Species-Dependent Regulation

“…Ortar et al described the preparation of 1 11 via (−)-menthylamine (1R,2S,5R)-2-isopropyl-5-methylcyclohexan-1-amine) using methodology by Schopohl and colleagues, 18 followed by EDCI/HOBt-assisted amidation. However, the absolute stereochemistry of (−)-menthylamine was not confirmed to be consistent with the structure reported by the latter group, who reported its X-ray crystal structure via incorporation into a caffeine complex.…”

“…However, the absolute stereochemistry of (−)-menthylamine was not confirmed to be consistent with the structure reported by the latter group, who reported its X-ray crystal structure via incorporation into a caffeine complex. 19 We resynthesized (−)-menthylamine 18 starting from L-menthone I-1 (Scheme 1). We prepared oxime I-2 using standard conditions from I-1 (95% yield), followed by Bouveault−Blanc reduction to I-3 in quantitative yield.…”

Derivatives of (–)‐Isosteviol with Expanded Ring D and Various Oxygen Functionalities

“…[6] Such architectures exhibiting a convergent concave geometry are all-syn functionalized triphenylene ketals. [9] For the potential application of these supramolecular scaffolds, defined stereoinformation on the backbone is crucial. [7] Chiral modification of such structures provided supramolecular clefts that enabled enantiofacial differentiation of the substrate, [8] but the synthesis required the installation of optically pure sterically congested moieties in the periphery.…”