Total Syntheses of (+)‐Villocarine A, (−)‐Apogeissoschizine, and (+)‐Geissoschizine DOI Open Access

Jukiya Sakamoto,

Mariko Kitajima,

Hayato Ishikawa

и другие.

Chemistry - A European Journal, Год журнала: 2023, Номер 29(18)

Опубликована: Янв. 21, 2023

Total syntheses of geissoschizine-type monoterpenoid indole alkaloids (MTIAs) are reported. An intramolecular Pictet-Spengler cyclization was developed for the selective construction 3R stereocenter. The first total synthesis (+)-villocarine A then achieved. Furthermore, highly strained (-)-apogeissoschizine also accomplished in an aza-Michael cyclization/E1cB elimination/stereoselective olefin isomerization sequence. Finally, (+)-geissoschizine, a common biosynthetic intermediate MTIAs, obtained from apogeissoschizine through ring-opening along with release ring strain.

Язык: Английский

Total Syntheses of (+)‐Villocarine A, (−)‐Apogeissoschizine, and (+)‐Geissoschizine DOI Open Access

Jukiya Sakamoto,

Mariko Kitajima,

Hayato Ishikawa

и другие.

Chemistry - A European Journal, Год журнала: 2023, Номер 29(18)

Опубликована: Янв. 21, 2023

Total syntheses of geissoschizine-type monoterpenoid indole alkaloids (MTIAs) are reported. An intramolecular Pictet-Spengler cyclization was developed for the selective construction 3R stereocenter. The first total synthesis (+)-villocarine A then achieved. Furthermore, highly strained (-)-apogeissoschizine also accomplished in an aza-Michael cyclization/E1cB elimination/stereoselective olefin isomerization sequence. Finally, (+)-geissoschizine, a common biosynthetic intermediate MTIAs, obtained from apogeissoschizine through ring-opening along with release ring strain.

Язык: Английский

Процитировано

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