Aminocyclohexane differences

Larsson, O. M., Johnston, G. A. R., and Schousboe, A. (1983) Differences in uptake kinetics of cis-3-aminocyclohexane carboxylic acid into neurons and astrocytes in primary cultures. 

For aminocyclohexane, the experimental value for the energy difference between the axial and equatorial conformer is 1.49 kcal/mol with the equatorial conformer as the most stable one [46]. In Fig. 9 it is shown that AMBER predicts the axial... 

In 2001, Funk reported a synthesis of ( )-FR901483 using an approach very different from those described previously, taking advantage of his amidoacrolein cycloaddition methodology to prepare 1 -alkyl-1 -aminocyclohexane derivatives, starting the synthesis from acyclic compounds. Moreover, Funk neither uses tyrosine derivatives nor needs an inversion at C(9) to install the phosphate unit. In Funk s retro synthetic analysis, shown in Scheme 23, he envisaged that lactam 60 possessed the necessary functionality for the introduction of the C(6) p-methoxy benzyl and C(3) methylamino substituents via enolate alkylation and amination reactions, respectively. 

A different approach using alkene derivatives involved allylic substitution reactions. Ethyl cyclohex-3-en-l-carboxylate (7.51) reacted with N-bromosuccin-imide to give 7.52.26 This allowed reaction with potassium phthalimide to give 7.53 in an overall yield of 41%. Catalytic hydrogenation and treatment with methylamine led to ds-3-aminocyclohexane-l-carboxylic acid, 7.22.26... 

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