Total syntheses and stereochemical reassignments of mollenines A and B. Issue 16 (1st September 2018)

• Record Type: Journal Article
• Authors: Shiomi, Shinya; Wada, Kohei; Umeda, Yuhei; Kato, Hikaru; Tsukamoto, Sachiko; Ishikawa, Hayato
• Is Part Of: Bioorganic & medicinal chemistry letters. Volume 28:Issue 16(2018)
• Page Start: 2766
• Page End: 2769
• Publication Date: 2018-09-01
• Subjects: Mollenine A -- Mollenine B -- Bioinspired reaction -- Total synthesis -- Dioxomorpholine; Bioorganic chemistry -- Periodicals; Pharmaceutical chemistry -- Periodicals; 572
• DOI: 10.1016/j.bmcl.2018.01.065
• Languages: English
• ISSNs: 0960-894X

Abstract

Graphical abstract: Abstract: Total syntheses of prenylated pyrrolidinoindoline alkaloids, (−)-mollenines A [(−)-1 ′] and B (2 ′), were accomplished via three- and four-step sequences including a bioinspired indole prenylation reaction followed by dioxomorpholine ring formation. Then, the stereochemistry of mollenines A and B was reassigned to 3 S, 6 S, 14 S, 16 S by analysis of spectroscopic data and chemical syntheses with different approaches along with the comparison of calculated and experimental ECD spectra. In addition, a thermodynamically controlled epimerization reaction on the dioxomorpholine ring was observed in our synthesis.