Conformation and Absolute Configuration of Naturally Occurring Parvifoline and Several Synthetic Derivatives

Joseph‐Nathan, Pedro; R, Hernández-Medel Mdel; Martínez, Emilia García; Rojas-Gardida, Mirna; Cm, Cerda

doi:10.1021/np50058a004

Cited by 26 publications

(10 citation statements)

References 14 publications

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“…Fore xample,o xidative cleavage of the tetrasubstituted double bond in these products can lead to the formation of eight-membered-ring-fused compounds,w hich are widely observed in natural products and advanced materials. [17] As shown in Scheme 4, at hree-step procedure,i ncluding Luche reduction, esterification, and oxidative cleavage of 2a gave eight-membered-ring-fused tricyclic product 6 in good yield. Thetwo carbonyl functionalities of 6 also allow ahigh degree of freedom for additional transformations if needed.…”

mentioning

confidence: 99%

Gold(I)‐Catalyzed Tandem Transformation with Diynes: Rapid Access to Linear Cyclopentenone‐Fused Polycyclic Molecules

Chen

Zhou

et al. 2015

Angew Chem Int Ed

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An efficient and convenient synthesis of useful linear cyclopentenone-fused polycyclic compounds has been achieved through a novel gold(I)-catalyzed transformation of diynes. The method demonstrates high product yields and tolerates of a wide variety of important functional groups. Gold-vinylidene formation, methoxy group migration, and Nazarov-type cyclization are proposed to be the key steps in the reaction pathway. The synthetic utility of this method is demonstrated by converting the product to eight-membered-ring-fused compound.

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confidence: 99%

Gold(I)‐Catalyzed Tandem Transformation with Diynes: Rapid Access to Linear Cyclopentenone‐Fused Polycyclic Molecules

Chen

Zhou

et al. 2015

Angew Chem Int Ed

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“…Eight‐membered rings combined with an aromatic skeleton, a class of fused eight‐membered compounds, have attracted considerable attention 1. 2 Such units have been found in various natural products as well as in pharmacologically active substances:3, 4 Iprindole ( 1 ),5 the first second‐generation antidepressant (TCA), and jolynamine ( 2 ),6 which was isolated from a dark brown alga belonging to the family Scytosiphonaceae, contain a cycloocta[ b ]indole skeleton (Figure 1). Very limited methods, especially those involving the unfavorable formation of eight‐membered rings, have been developed for the synthesis of these type of products 2b,c,d.…”

Section: Methodsmentioning

confidence: 99%

A Sensitive and Selective Fluorescent Probe for Cysteine Based on a New Response‐Assisted Electrostatic Attraction Strategy: The Role of Spatial Charge Configuration

Zhou

Jin

Sun

et al. 2013

Chemistry A European J

101

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A new strategy for fast fluorescent detection of cysteine (Cys), based on a response-assisted electrostatic attraction, is demonstrated. By utilizing this strategy, we designed and synthesized three fluorescent probes for the specific detection of Cys under actual physiological conditions. The probe m-CP, a coumarin fluorophore conjugated with a substituted methyl pyridinium group through an unsaturated ketone unit, showed highly selective and sensitive detection for cysteine (Cys) over homocysteine (Hcy) and glutathione (GSH). The kinetic analysis indicated that the sensing process was highly accelerated (a response time less than 1 min) by the response-assisted electrostatic attraction. More importantly, control experiments with isomeric probes first demonstrated that the spatial charge configuration of the probe played an important role in Cys-preferred selectivity and kinetic rate acceleration. Furthermore, the practical utility of the probe m-CP in the fluorescent labeling of Cys residues within proteins was demonstrated. Finally, these probes were employed in living cell imaging with HeLa cells, in which it displayed satisfactory cell permeability and enabled us to distinguish active thiols in the cytoplasm, nucleus, and mitochondria.

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“…Cycloocta[ b ]indole is a tricyclic heterocycle, and its cyclooctane ring shares two carbons of indole at the C2 and C3 positions. The cycloocta[ b ]indole skeleton is seen in many natural and biologically active compounds For example, iprindole (Figure ) has been used for the treatment of depression, and talcarpine is a macroline alkaloid, which is a family of more than 150 compounds with potent hypotensive and antibiotic activities. While cycloocta[ b ]indoles have been shown to have attractive biological activities, there are few examples of the synthesis of the skeleton .…”

Section: Introductionmentioning

confidence: 99%

One‐Pot Synthesis of Cycloocta[b]indole Through Formal [5+3] Cycloaddition Using Donor–Acceptor Cyclopropanes

et al. 2019

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A new approach to cycloocta[b]indole through formal [5+3] cycloaddition was developed. This methodology was realized by using an indole derivative as a C5 unit and a cyclopropane derivative as a C3 unit. These two units have both donor and acceptor properties. Two carbon–carbon bonds were formed stepwise by the successive addition of a Lewis acidic catalyst and a Brønsted base. The reaction could be performed as a one‐pot process. Optically active cycloocta[b]indole was also synthesized by using this methodology with a chiral cyclopropane as a C3 substrate.

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Conformation and Absolute Configuration of Naturally Occurring Parvifoline and Several Synthetic Derivatives

Cited by 26 publications

References 14 publications

Gold(I)‐Catalyzed Tandem Transformation with Diynes: Rapid Access to Linear Cyclopentenone‐Fused Polycyclic Molecules

Gold(I)‐Catalyzed Tandem Transformation with Diynes: Rapid Access to Linear Cyclopentenone‐Fused Polycyclic Molecules

A Sensitive and Selective Fluorescent Probe for Cysteine Based on a New Response‐Assisted Electrostatic Attraction Strategy: The Role of Spatial Charge Configuration

One‐Pot Synthesis of Cycloocta[b]indole Through Formal [5+3] Cycloaddition Using Donor–Acceptor Cyclopropanes

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