An efficient approach to the asymmetric total synthesis of (–)-anisodine

Selective separation and purification of highly polar basic compounds using a silica-based strong cation exchange stationary phase

“…This study is the first to detect its presence in S. tangutica Maxim. 13 C NMR spectral data were in agreement with those of anisodine [42].…”

Total Synthesis of (±)‐Scopolamine: Challenges of the Tropane Ring

“…The concentration of scopolamine in these species is rather low. [3] Only one total synthesis of scopolamine has been described so far, [6] even though precursors to the final product have been reported, [7] as in the syntheses of related alkaloids such as anisodine (3), [8,9] or scopine. [10] In the course of our were each independently evaluated for their utility in constructing the tropane core.…”

“…We reasoned that 6,7-dehydrotropine (4) could serve as a key, and potentially broadly applicable, intermediate since the oxirane ring is likely to cause side reactions when present at an early stage of the synthesis. Compound 4 could be used as a common precursor for several alkaloids such as scopolamine (2), anisodine (3), [8] hyoscyamine (5), or anisodamine (6) (Figure 2). Herein, we describe the total synthesis of scopolamine (2) from key intermediate 4.…”

“…The solution was refluxed for 4 h. After cooling, 6 M HCl (0.33 mL) was added and the reaction was stirred at room temp. for 13 h. K 2 CO 3 was added (until pH [7][8] [8][9]) and the product was extracted with CHCl 3 (3 × 2 mL). The combined organic layers were dried with Na 2 SO 4 , filtered and concentrated under reduced pressure.…”

Cage-like amino alcohols. synthesis, reactions, and application

“…Amino alcohols are found in nature or are structurally related to naturally occurring compounds [1][2][3][4][5][6][7][8].…”