Preparation of pyrrolizinone derivatives via sequential transformations of cyclic allyl imides: synthesis of quinolactacide and marinamide

Abstract

A facile synthetic route has been developed for the preparation of pyrrolizinone derivatives employing N-allyl imides as starting materials. The nucleophilic addition of a vinyl Grignard reagent/RCM/elimination sequence afforded pyrrolizinones in good yields and has been applied for the preparation of naturally occurring quinolactacide and marinamide.

Iron‐Catalyzed Radical Relay Enabling the Modular Synthesis of Fused Pyridines from Alkyne‐Tethered Oximes and Alkenes

“… [19] In addition, a polycyclic N‐heterocycle 6 was achieved from 3 ag by means of nucleophilic addition and olefin metathesis (Scheme 4 c). [20] 3 ak reacted with 3,3‐dimethyl‐1‐butene by a rhodium‐catalyzed C−H functionalization to furnish the alkylated product 7 (Scheme 4 d). [21] In the case of 3 qa , a copper‐catalyzed click reaction with TsN 3 produced a triazole compound in a quantitative yield (Scheme 4 e).…”

Iron‐Catalyzed Radical Relay Enabling the Modular Synthesis of Fused Pyridines from Alkyne‐Tethered Oximes and Alkenes

“…[19] In addition, apolycyclic N-heterocycle 6 was achieved from 3ag by means of nucleophilic addition and olefin metathesis (Scheme 4c). [20] 3ak reacted with 3,3-dimethyl-1-butene by ar hodium-catalyzed CÀHf unctionalization to furnish the alkylated product 7 (Scheme 4d). [21] In the case of 3qa, ac opper-catalyzed click reaction with TsN 3 produced at riazole compound in aquantitative yield (Scheme 4e).…”

Recent Advances for the Synthesis of N‐Unsubstituted Pyrroles

“…A very unusual transformation of Vinyl Sultam is presented in work [110] . Treatment of sultam 359 a with excess NaOEt resulted N−S bond cleavage affording two type of pyrroles: 360 a and 360 b (Scheme 120).…”

“…An interesting protocol of transformation of sulfones 351 a,b into pyrroles 358 a,b was presented by Fernanda M. Ribeiro Laia et al [109] The process involves electrocyclization, Claisen rearrangement, enolisation, 1,5-H shift and second electro- A very unusual transformation of Vinyl Sultam is presented in work. [110] Treatment of sultam 359 a with excess NaOEt resulted NÀ S bond cleavage affording two type of pyrroles: Several transformations of the pyrrolizinone derivatives 361 were carried out by Simic et al [111] The alkaline hydrolysis of 361 produced pyrrole derived carboxylic acid 362 in good yields (Scheme 121).…”