Hydrohalogenative aromatization of multiynes promoted by ruthenium alkylidene complexes

Karmakar, Rajdip; Wang, Kung Pern; Yun, Sang Young; Mamidipalli, Phani; Lee, Daesung

doi:10.1039/c6ob00524a

Cited by 24 publications

(14 citation statements)

References 67 publications

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“…Aside from the above-referenced syntheses, the total syntheses of (+)- 1 , 10,11 (+)- 2 , 12 (±)- 1 and (±)- 2 , 11,13,14,15,16,17,18 (+)- 3 , 11 (±)- 3 , 13,19 and (±)- 6 – 8 have been achieved. 13,19,20 A formal synthesis of (±)- 3 has also been reported, 21 and all total syntheses of trikentrin-herbindole family, up to 2009, have been reviewed. 22…”

Section: Introductionmentioning

confidence: 99%

Six Trikentrin-like Cyclopentanoindoles from Trikentrion flabelliforme. Absolute Structural Assignment by NMR and ECD

Salib

Molinski

2018

J. Org. Chem.

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Six new cyclopenta[g]indoles were isolated from a West Australian sponge, Trikentrion flabelliforme Hentschel, 1912, and their structures elucidated by integrated spectroscopic analysis. The compounds are analogues of previously described trikentrins, herbindoles, and trikentramides from related Axinellid sponges. The assignment of absolute configuration of the new compounds was carried out largely by comparative analysis of specific rotation, calculated and measured ECD, and exploiting van't Hoff's principle of optical superposition. Five of the new compounds were chemically interconverted to establish their stereochemical relationships, leading to a simple chiroptical mnemonic for assignment of the this family of chiral indoles. The first biosynthetic hypothesis is advanced to explain the origin of the trikentrin-herbinole family and proposes a pyrrole-carboxylic thioester-initiated polyketide synthase mechanism.

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Section: Introductionmentioning

confidence: 99%

Six Trikentrin-like Cyclopentanoindoles from Trikentrion flabelliforme. Absolute Structural Assignment by NMR and ECD

Salib

Molinski

2018

J. Org. Chem.

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“…Here we describe a new strategy for carbazole assembly that capitalizes on the hexadehydro-Diels–Alder (HDDA) cascade . The process involves a sequential net 4+2 cycloisomerization reaction between a 1,3-diyne and a diynophile to produce a benzyne intermediate, followed by one of several different modes of trapping reactions. − This cascade constitutes a powerful and versatile strategy for synthesis of benzenoid derivatives in which the benzene ring itself has been assembled in de novo fashion from the six reacting alkyne carbon atoms. The purely thermal nature of the reaction conditions lends itself to the discovery of new types of aryne trapping reactions that can be complementary to those possible with arynes generated by conventional means.…”

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confidence: 99%

Hexadehydro-Diels–Alder (HDDA)-Enabled Carbazolyne Chemistry: Single Step, de Novo Construction of the Pyranocarbazole Core of Alkaloids of the Murraya koenigii (Curry Tree) Family

Wang

Hoye

2016

J. Am. Chem. Soc.

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Here we report the use of the hexadehydro-Diels–Alder (HDDA) reaction for the de novo construction of a benzenoid ring in fused polycyclic heteroaromatic carbazole (i.e., [2,3]-benzoindole) skeletons. The strategy allows creation of highly substituted benzenoids. We also describe the HDDA-enabled chemical synthesis of the natural product alkaloids mahanimbine and koenidine. Trapping of the intermediate carbazolyne with a conjugated enal–proceeding through formal [2+2] cycloaddition, 4π-electrocyclic ring-opening, and 6π-electrocyclic ring-closing events—constitutes a robust method for producing pyranocarbazoles.

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“…The authors observed that the microwave irradiation enhanced the reactivity; however, it did not affect the regioselectivity [224] . Amide‐tethered diynes, [225] N ‐benzenesulfonamide 1,6‐diynes, [226] and bis‐1,3‐diynes [227] were used as efficient substrates to [2+2+2] cycloisomerization reactions to give the corresponding isoindolines in good yields.…”

Section: Synthesis Of Isoindolinesmentioning

confidence: 99%

Recent Developments in the Cyclization of Alkynes and Nitrogen Compounds for the Synthesis of Indole Derivatives

Neto

Zeni

2021

Asian J Org Chem

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This review is intended to highlight the most useful approaches for the synthesis of indole derivatives (azaindoles, carbazoles, carbolines, indazoles, 3H-indoles, indolines, indolizines, isoindoles, and isoindolines), which were described by using transition-metal catalyzed cyclization reactions of alkynes and nitrogen compounds. The methodologies carried out under metal-free conditions will also be illustrated herein. This review will cover the data published mostly in the past decade. Synthesis of 6-AzaindolesAzaindoles, although rare in nature, have attracted a significant attention because some synthetic structures containing this nucleus exhibit biological activities. [17] The synthetic methods describing the preparation of azaindoles are limited. Usually their synthesis was achieved from the cyclization reaction of substrates containing aminopyridines. [18] Transition Metal-Free Synthesis of 6-AzaindolesWe have nominated two methodologies for the preparation of 6-azaindoles, which were developed using alkynes and nitrogen compounds in a metal-free protocol. In the first, an electrophilic cyclization condition, using iodine as an electrophilic source, was applied to 2-(azidomethyl)-3-alkynyl-pyrroles in the preparation of 4-iodo-6-azaindoles 1 (Scheme 1, eq 1). [19] The second approach described the preparation of 2,5-disubstituted 6azaindoles 2 from base-catalyzed intramolecular cyclization of 2-(azidomethyl)-3-alkynyl-pyrroles (Scheme 1, eq 2). [20] 3. Synthesis of 7-Azaindoles Transition Metal-Catalyzed Synthesis of 7-Azaindoles Silver-Catalyzed Synthesis of 7-AzaindolesSilver-catalyzed cyclization reactions of alkynes constitute powerful strategies for the construction of heterocycles. In particular, the 7-azaindoles could be obtained by these approaches. A general method for the preparation of aryl-[a] Dr. J.

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Hydrohalogenative aromatization of multiynes promoted by ruthenium alkylidene complexes

Cited by 24 publications

References 67 publications

Six Trikentrin-like Cyclopentanoindoles from Trikentrion flabelliforme. Absolute Structural Assignment by NMR and ECD

Six Trikentrin-like Cyclopentanoindoles from Trikentrion flabelliforme. Absolute Structural Assignment by NMR and ECD

Hexadehydro-Diels–Alder (HDDA)-Enabled Carbazolyne Chemistry: Single Step, de Novo Construction of the Pyranocarbazole Core of Alkaloids of the Murraya koenigii (Curry Tree) Family

Recent Developments in the Cyclization of Alkynes and Nitrogen Compounds for the Synthesis of Indole Derivatives

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