Cover Feature: Selective Deconstructive Lactamization of the Indolo[2,3‐<i>a</i>]quinolizine Skeleton for the Total Synthesis of (+) and (−)‐Cuscutamine (Eur. J. Org. Chem. 32/2022)

Recoba‐Torres, Adriana; Cruz‐Gregorio, Silvano; Quintero, Leticia; Sandoval‐Lira, Jacinto; Romero‐Ibañez, Julio; Sartillo‐Piscil, Fernando

doi:10.1002/ejoc.202200953

Cited by 2 publications

(2 citation statements)

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“…The authors have cited additional references within the Supporting Information. [19][20][21][22][23][24]…”

Section: Discussionmentioning

confidence: 99%

Indole C5‐Selective Bromination of Indolo[2,3‐a]quinolizidine Alkaloids via In Situ‐Generated Indoline Intermediate

Yoshimura,

Sakamoto,

Kitajima

et al. 2024

Chemistry A European J

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There are many indole alkaloids that contain diverse functional groups attached to the benzene ring on the indole core. Promising biological activities of these alkaloids have been reported. Herein, we report the indole C5‐selective bromination of indolo[2,3‐a]quinolizidine alkaloids by adding nearly equimolar amounts of Br3·PyH and HCl in MeOH. The resulting reaction plausibly proceeds through an indoline intermediate by the nucleophilic addition of MeOH to the C3‐brominated indolenine intermediate. Data support the intermediacy of a C3‐, C5‐dibrominated indolenine intermediate as a brominating agent. These conditions demonstrate excellent selectivity for indole C5 bromination of natural products and their derivatives. Thus, these simple, mild, and metal‐free conditions allow for selective, late‐stage bromination followed by further chemical modifications. The utility of the brominated product prepared from naturally occurring yohimbine was demonstrated through various derivatizations, including a bioinspired heterodimerization reaction.

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“…The authors have cited additional references within the Supporting Information. [19][20][21][22][23][24]…”

Section: Discussionmentioning

confidence: 99%

Indole C5‐Selective Bromination of Indolo[2,3‐a]quinolizidine Alkaloids via In Situ‐Generated Indoline Intermediate

Yoshimura,

Sakamoto,

Kitajima

et al. 2024

Chemistry A European J

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“…In 2022, Recoba‐Torres and co‐workers developed the synthesis of indolizinoindoles 306 from indolo[2,3 ‐a ]quinolizine 304 . Scheme 91 shows the preparation of (±)‐ Cuscutamine 307 from L ‐tryptophan [106] …”

Section: Approaches To the Synthesis Of Indolizinoindolesmentioning

confidence: 99%

Synthetic Strategies for the Construction of Indolizines and Indolizine‐fused Compounds: Thienoindolizines and Indolizinoindoles

Nevskaya,

Zinoveva,

Van der Eycken

et al. 2023

Asian J Org Chem

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This paper provides a review on various methodologies developed for the synthesis of different indolizine derivatives and an overview of their application. These include thienoindolizine and indolizino[8,7‐b]indole derivatives. The indolizine nucleus occurs as privileged scaffold of many natural and synthetic molecules with significant biological activity. Fused‐indolizines such as thienoindolizines and indolizinoindole derivatives are of great interest, due to their antitumor, antimicrobial and enzyme inhibitor activity. Because of their widespread use in chemical, medicinal, biological, and materials science research, indolizines and their fused derivatives are attractive synthetic targets in the search for efficient methods for their construction.

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Cover Feature: Selective Deconstructive Lactamization of the Indolo[2,3‐a]quinolizine Skeleton for the Total Synthesis of (+) and (−)‐Cuscutamine (Eur. J. Org. Chem. 32/2022)

Cited by 2 publications

References 0 publications

Indole C5‐Selective Bromination of Indolo[2,3‐a]quinolizidine Alkaloids via In Situ‐Generated Indoline Intermediate

Indole C5‐Selective Bromination of Indolo[2,3‐a]quinolizidine Alkaloids via In Situ‐Generated Indoline Intermediate

Synthetic Strategies for the Construction of Indolizines and Indolizine‐fused Compounds: Thienoindolizines and Indolizinoindoles

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