Asymmetric Synthesis of (+)- and (-)-Eptazocine via an Enzymatic Reaction

Asymmetric Syntheses of (−)‐Pentazocine and (−)‐Eptazocine through an Aza‐Prins Cyclization

“…Finally, deprotection of the tosyl group, N‐methylation with formaldehyde, and demethylation with BBr 3 afforded (−)‐eptazocine in 57 % yield over three steps. 1 H and 13 C NMR spectra and other physical data of our synthetic compound 2 were all in good agreement with those reported in the literature 4a,c…”

“…[1] Structural modification can reduce this problem to a considerable extent, [2] for example, the clinically used (À)-pentazocine (1) and (À)-eptazocine (2) are useful alternatives (Figure 1). Both (À)-pentazocine [3] and (À)-eptazocine [4] have attracted considerable interest to synthetic chemists owing to their prominent or potential pharmacological activities, and several syntheses of these compounds have been achieved. In contrast, there is no common strategy, that, is not only suitable for synthesis of (À)-pentazocine, but also for synthesis of (À)-eptazocine, despite their similar structures.…”

Comparing the Stereoselective Biooxidation of Cyclobutanones by Recombinant Strains Expressing Bacterial Baeyer–Villiger Monooxygenases

“…Accessibility of antagonistic analgesics like eptazocine, [13] GABA receptor inhibitors, [12b] the synthesis of b-amino acids like b-proline, [12c] and structurally related lignans [14] are within their area of application. Scheme 1 gives a summary of the importance of antipodal benzyl butyrolactones 2f-i in the synthesis of various lignans.…”

Synthesis of maculalactone A and derivatives for environmental fate tracking studies

“…Malonate, 18, was synthesised based on a reported procedure 43 and converted to its potassium salt, 19, at reduced temperature to prevent decarboxylation. First, however, the appropriate position for the modifications had to be identified in a structure-activity relationship study (SAR).…”