A Concise Approach to Paxilline Indole Diterpenes

• Published in: Journal of the American Chemical Society Vol. 137; no. 49; pp. 15410 - 15413
• Main Authors: George, David T, Kuenstner, Eric J, Pronin, Sergey V
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 16.12.2015; Amer Chemical Soc
• Subjects: Chemistry; Chemistry, Multidisciplinary; Diterpenes - chemistry; diterpenoids; Indoles - chemistry; ketones; Molecular Structure; paxilline; Physical Sciences; Science & Technology; Terpenes - chemistry; TERTIARY ALCOHOLS; ENOL ETHERS; BIOSYNTHESIS; CONSTRUCTION; ALPHA; QUATERNARY CARBONS; 2ND-GENERATION SYNTHESIS; CONJUGATE ADDITION; CARBOXYLIC-ACIDS; ALKALOIDS

A synthetic approach to paxilline indole diterpenes is described. The route to the penta­cyclic core relies on a new regio­selective alkenyl­ation of ketones and a tandem radical addition–aldol reaction sequence to access vicinal quaternary stereo­centers. Emindole SB, the simplest member of the fam...