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A speedy route to sterically encumbered, benzene-fused derivatives of privileged, naturally occurring hexahydropyrrolo[1,2-b]isoquinoline.

ABSTRACT: A series of 15 benzene-fused hexahydropyrrolo[1,2-b]isoquinolonic acids with substantial degree of steric encumbrance has been prepared via a novel variant of the Castagnoli-Cushman reaction of homophthalic anhydride (HPA) and various indolenines. The employment of a special kind of a cyclic imine component reaction allowed, for the first time, isolating a Mannich-type adduct between HPA and an imine component which has been postulated but never obtained in similar reactions.

SUBMITTER: Bakulina O

PROVIDER: S-EPMC5530605 | biostudies-literature | 2017

REPOSITORIES: biostudies-literature

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A speedy route to sterically encumbered, benzene-fused derivatives of privileged, naturally occurring hexahydropyrrolo[1,2-<i>b</i>]isoquinoline.

Bakulina Olga O Ivanov Alexander A Suslonov Vitalii V Dar'in Dmitry D Krasavin Mikhail M

Beilstein journal of organic chemistry 20170718

A series of 15 benzene-fused hexahydropyrrolo[1,2-<i>b</i>]isoquinolonic acids with substantial degree of steric encumbrance has been prepared via a novel variant of the Castagnoli-Cushman reaction of homophthalic anhydride (HPA) and various indolenines. The employment of a special kind of a cyclic imine component reaction allowed, for the first time, isolating a Mannich-type adduct between HPA and an imine component which has been postulated but never obtained in similar reactions. ...[more]

PMID: 28781707

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