Synthetic Approaches to Enantiomerically Pure 8-Azabicyclo[3.2.1]octane Derivatives

Molecular Basis for β‐Glucosidase Inhibition by Ring‐Modified Calystegine Analogues

“…Despite their similar inhibitory potential and chemical structure, however, the thermodynamic data show significant differences in the enthalpic and entropic contributions to that the longer alkyl chain might be involved in displacement of more water molecules in the active site. Both thermodynamic signatures are different to that observed for the parent calystegine B 2 1, which has a small enthalpy term that is offset by a large favourable entropic contribution (DH a = À2.9 kcal mol À1 ; TDS a = + 4.5 kcal mol À1 ). [10] X-ray data for TmGH1 in complex with 9 were collected to a resolution of 1.90 (Table 2) and refined to a final R cryst of 0.20 and R free of 0.24.…”

“…[2,3] Similar to the well-studied polyhydroxypiperidine, indolizidine, pyrrolidine and pyrrolizidine-type iminocyclitols, [4] calystegines exhibit potent glycoside hydrolase (glycosidase) inhibitory properties. Given the broad range of biological events in which glycosidases are involved, inhibitors of these enzymes have potential in therapies that are targeted at, for example, cancer, [5] viral infections, [6] tuberculosis, [7] diabetes [8] and glycosphingolipid storage disorders.…”

Determination of the N-invertomer stereochemistry in N-substituted nortropanones and norgranatanones using computational and NMR methods

“…Some of the most synthetically useful transformations of tropane-and granatane-derived ketones are the diastereoselective and enantioselective aldol reactions [15]. Tropinone has been successfully used in this capacity for the synthesis of several bioactive derivatives, such as cocaine [16] and its analogues [6,7], as well as of several other alkaloids [17][18][19][20][21].…”

A concise stereoselective synthesis of (−)-erycibelline

“…Due to their unique structures and promising pharmaceutical applications, 2 tropane alkaloids continue to draw the attention of both synthetic and medicinal chemists since their first discovery in the mid 19th century. 3 (-)-Erycibelline 4 ( Fig. 1) is the first naturally occurring dihydroxynortropane alkaloid isolated from the Chinese herb medicine Erycibe elliptilimba Merr.…”