Synthetic studies related to the akuammiline alkaloids

Abstract

6-Ethyl-2,3-dihydro-1-phenyl-1H-pyrrolizine 19 and 1-(2-aminophenyl)-6-ethyl-2,3-dihydro-1H-pyrrolizine 30 were synthesized starting from the pyrroles 4-acetylpyrrol-2-yl phenyl ketone 13 and 4-acetylpyrrol-2-yl 2-(dimethylaminomethylenamino)phenyl ketone 26, respectively, using vinyltriphenylphosphonium bromide in an intramolecular Wittig reaction for the formation of the second five-membered ring.

Design and synthesis of quinazolin-4-one derivatives as potential anticancer agents and investigation of their interaction with RecQ helicases

“…The synthetic pathways for the designed compounds are depicted in Scheme 1 and Scheme 2. In Scheme 1, cyclization reaction of anthranilic acid (1) and benzoyl chloride under basic conditions as reported in references, [24,25] yielded 2-phenyl-4H-benzoxazin-4-one (2). Upon reaction of intermediate 2 with 99% hydrazine hydrate in ethanol at 80 °C, an unexpected formation of the open-ring structure N- (2-(hydrazinecarbonyl)phenyl)benzamide (3) was observed.…”

“…The combined crops were dried. [24,25] The product was obtained as a white powder ( [1,3]dioxol-5-ylmethylene)hydrazine-1-carbonyl)phenyl)benzamide 4a…”

Access to the Akuammiline Family of Alkaloids: Total Synthesis of (+)-Scholarisine A

“…Alkaloids that derive biosynthetically via cyclization of geissoschizine ( 5 ), forming a bond between C-7 and C-16, are considered members of the akuammiline alkaloid family (Figure ) . Akuammiline ( 7 ), the progenitor from which this class derives the name, was first characterized in 1932 .…”

A 7-Step Formal Asymmetric Total Synthesis of Strictamine via an Asymmetric Propargylation and Metal-Mediated Cyclization

“… Some of its members have been known for over 125 years, and several have shown promising biological activity . Given such a profile, it is unsurprising that numerous endeavors have sought to access them over the past 4 decades; despite much effort, however, it is only within recent years that laboratory chemical synthesis has overcome their challenges, with successful total syntheses of scholarisine A ( 1 ), aspidophylline A ( 2 ), picrinine ( 3 ), vincorine ( 4 ), aspidodasycarpine ( 5 ), and others having been reported; one is from our group…”