Total syntheses of the dipyrrolobenzoquinone (+)-terreusinone enabled by an evaluation of 4-methylpent-1-yn-3-ols in the Larock indole synthesis

Wang, Christy; Sperry, Jonathan

doi:10.1016/j.tet.2013.04.025

Cited by 25 publications

(13 citation statements)

References 143 publications

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“…The total synthesis of (+)-53 was accomplished by a copper-and amine-free double Sonogashira reaction followed by hydroamination to simultaneously install both indole rings 54 (Scheme 6). 30,31 Indoloquinoline alkaloids have received signicant attention because of their striking biological activities and their intriguing structures. A simple method for the synthesis of quindoline (56), indolo[3,2-b]quinoline alkaloid, was reported by two groups.…”

Section: Non-tryptaminesmentioning

confidence: 99%

Simple indole alkaloids and those with a nonrearranged monoterpenoid unit

Ishikura,

Abe,

Choshi

et al. 2015

Nat. Prod. Rep.

214

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Section: Non-tryptaminesmentioning

confidence: 99%

Simple indole alkaloids and those with a nonrearranged monoterpenoid unit

Ishikura,

Abe,

Choshi

et al. 2015

Nat. Prod. Rep.

214

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“…Several elegant synthetic protocols for the preparations of indolebenzoquinones have been well documented and are listed below (Scheme ). The first and the most commonly used method is direct oxidation of corresponding indoles by Fremy's salt ,. One of the disadvantages of this method is the potential generation of side products having carbonyl groups in various locations and with diverse quantities.…”

Section: Introductionmentioning

confidence: 99%

Palladium-Catalyzed C-H Functionalization of Amido-Substitued 1,4-Napthoquinone in the Presence of Amines toward the Formation of Pyrroles and Imidazoles

Chen

Hong

2017

ChemistrySelect

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Transition metal‐catalyzed ortho‐ C−H functionalization of amido‐substituted 1,4‐naphthoquinone, 3, in the presence of Pd(OAc)2 and tertiary amines led to the formations of 4 with newly generated pyrrole rings. Similar reactions were carried out with primary amines and yielded 5, having imidazole rings, as well as amination products 6. In the cases of reacting with secondary amines, the route for the formations of 4‐like, rather than 5‐type, products were prevailed. As revealed from the crystal structures of 4_Bu, 6_Bu, 6_Cy, and 4_Cy, cyclization processes indeed took place to form pyrrole and imidazole rings, respectively, which are fused to the former naphthoquinone framework. The crystal structure of 5_Cy shows that it is a product from amination reaction. Similar reaction was carried out using PCy3 as the phosphine source and an unexpected product 7 was obtained. The crystal structure of 7 exhibits that the moiety of PCy3 attaches to the framework of the former naphthoquinone and brings about a new P=C double bond. In addition, the amide fragment of 3 is hydrolyzed and reduced and forms C=N double bond. Here, distinct reactivity of amines from that of phosphines in this type of reactions have been manifested.

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“…To a solution of indole 20 in THF at 0°C, tetra ‐butylammonium fluoride (TBAF) was added, and the reaction solution was warmed to room temperature to provide compound 23 . Further, [(2‐biphenyl) di‐ tert ‐butylphosphine]gold(I) hexafluoroantimonate was mixed and heated at 60°C to afford compound 24 , which undergoes oxidation to afford (+)‐terreusinone, a pyrroloindole derivative 25 as shown in Scheme .…”

Section: Synthetic Strategiesmentioning

confidence: 99%

“…Further, [(2-biphenyl) di-tert-butylphosphine]gold(I) hexafluoroantimonate was mixed and heated at 60°C to afford compound 24, which undergoes oxidation to afford (+)-terreusinone, a pyrroloindole derivative 25 as shown in Scheme 5 [17].…”

Section: Synthetic Strategiesmentioning

confidence: 99%

Diversified Synthetic Strategies for Pyrroloindoles: An Overview

Manjal

Pathania

Bhatia

et al. 2019

Journal of Heterocyclic Chem

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In current scenario, heterocyclic compounds' role in medicinal chemistry has been tremendously increased as they possess wide number of pharmacological activities. One of the common heterocycles include indole skeleton with well‐established biological significance in field of medicinal chemistry. Fusion of indole nucleus with pyrrole heterocycle constitutes pyrroloindole scaffold, which further modifies the existing properties of indole alone. Pyrroloindole is a privileged scaffold found in various types of bioactive entities including natural compounds and exhibits wide variety of pharmacological activities like muscle relaxant, antifungal, antitumor, and antibiotic. Therefore, it is considered as attractive template for drug discovery. From several years, numbers of synthetic strategies have been reported for the synthesis of pyrroloindole and its derivatives, including also natural compounds such as amauromine, yuremamine, and chimonanthines. Here, in this review, we have tried to compile various synthetic strategies of pyrroloindole and its derivatives.

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Total syntheses of the dipyrrolobenzoquinone (+)-terreusinone enabled by an evaluation of 4-methylpent-1-yn-3-ols in the Larock indole synthesis

Cited by 25 publications

References 143 publications

Simple indole alkaloids and those with a nonrearranged monoterpenoid unit

Simple indole alkaloids and those with a nonrearranged monoterpenoid unit

Palladium-Catalyzed C-H Functionalization of Amido-Substitued 1,4-Napthoquinone in the Presence of Amines toward the Formation of Pyrroles and Imidazoles

Diversified Synthetic Strategies for Pyrroloindoles: An Overview

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