Biomimetic and Concise Total Syntheses of Prenylated and Bicyclo[2.2.2]diazaoctane-Containing Indole Alkaloids Including Taichunamide A, Notoamide N and Versicolamide B

• Published in: Journal of organic chemistry Vol. 89; no. 17; pp. 12639 - 12650
• Main Authors: Xu, Zhongnan, Liang, Xin-Ting, White, Lorenzo V., Banwell, Martin G., Tan, Shen
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 06.09.2024; Amer Chemical Soc
• Subjects: Biomimetics; Chemistry; Chemistry, Organic; chlorination; condensation reactions; Cycloaddition Reaction; cycloaddition reactions; diketopiperazines; epoxidation reactions; hydrolysis; Indole Alkaloids - chemical synthesis; Indole Alkaloids - chemistry; indoles; Indoles - chemical synthesis; Indoles - chemistry; Lewis bases; Molecular Structure; organic chemistry; oxidation; Physical Sciences; Prenylation; Science & Technology; Stereoisomerism; (-)-VERSICOLAMIDE B; PRECURSOR; RING-SYSTEM; MARINE; BIOSYNTHESIS; STEPHACIDIN-A

Total syntheses of the title prenylated indole alkaloids together with seven others are reported. Biogenetic considerations have been employed in devising the reaction sequences leading to these targets with, in the opening stages, electrochemically-derived indole-3-carboxaldehyde 15 being subject t...