The Total Synthesis of Ipalbidine and Ipalbine

Abstract

Zusammenfussung. Eine Totalsynthese des Hexahydroindolizin-Alkaloids Ipalbidin (7) und seines P-D-Glucosids Ipalbin (1) wird beschricben. Dcr zentrale Syntheseschritt besteht aus ciner N-Acylierung des vinylogen Amidsystems 3, gefolgt von einer internen Kondensation zum penta-

Alkaloids

“…It is dextrorotatory, [α] 23 D + 32.5 • (ethanol). The structure was confirmed by the total synthesis from 2-methoxypyrroline and methyl acetoacetate [27]. The seeds of Ipomoea muricata, a plant grown in Senegal, affords ipomine (70) and ipalbidine (69).…”

“…Tobacco alkaloids, include nicotine (26), nicotyrine (27), and anabasine (28). Nicotine is the principal alkaloid from tobacco plants (genus Nicotiana).…”

“…Chromic acid oxidation gives nicotinic acid (29), whereas distillation from lime affords pyrrole and methylamine. Nicotyrine (27) is the corresponding tetradehydro compound, whereas anabasine (28) is an isomer of nicotine.…”

Five-, Six-, and Seven-membered Lactim Ethers. Methods of Synthesis and Chemical Properties. (Review)

“…γ-Butyrolactam (1), δ-valerolactam (2), and ε-caprolactam (3) and their derivatives are most often used as starting compounds for the production of lactim ethers.…”

“…The heating of lactams with dimethyl sulfate [2][3][4][5][6][7][8][9][10][11][12][13][14][15], or more rarely diethyl sulfate [4,5,[15][16][17], is the most widely used method for the synthesis of lactim ethers (Table 1).…”