Total Synthesis of (−)-Citreoisocoumarin, (−)-Citreoisocoumarinol, (−)-12-<i>epi</i>-Citreoisocoumarinol, and (−)-Mucorisocoumarins A and B Using a Gold(I)-Catalyzed Cyclization Strategy

Mallampudi, N. Arjunreddy; Choudhury, Utkal Mani; Mohapatra, Debendra K.

doi:10.1021/acs.joc.9b03278

Cited by 16 publications

(9 citation statements)

References 56 publications

(22 reference statements)

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“…A key step in this synthesis is a Pd(0)-catalyzed cross-coupling reaction between an aryl triflate (4), which already contained the spacer arm, and an appropriately functionalized arylboronic acid (6) (Scheme 1). The aryl triflate 4 was prepared in two steps from the readily available 1,3-benzodioxinone 1 [21,22]. First, an O-alkylation reaction with methyl 5-bromovalerate was performed under standard Williamson ether synthesis conditions.…”

Section: Hapten Design and Synthesismentioning

confidence: 99%

Assessment of the Optimum Linker Tethering Site of Alternariol Haptens for Antibody Generation and Immunoassay Development

Addante-Moya

Abad‐Somovilla

Abad‐Fuentes

et al. 2021

Toxins

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Immunochemical methods for mycotoxin analysis require antigens with well-defined structures and antibodies with outstanding binding properties. Immunoreagents for the mycotoxins alternariol and/or alternariol monomethyl ether have typically been obtained with chemically uncharacterized haptens, and antigen conjugates have most likely been prepared with mixtures of functionalized molecules. For the first time, total synthesis was performed, in the present study, to obtain two haptens with opposite linker attachment locations. The functionalized synthetic haptens were purified and deeply characterized by different spectrometric methods, allowing the preparation of bioconjugates with unequivocal structures. Direct and indirect competitive enzyme-linked immunosorbent assays, using homologous and heterologous conjugates, were employed to extensively evaluate the generated immunoreagents. Antibodies with high affinity were raised from conjugates of both haptens, and a structure-activity relationship between the synthetic haptens and the specificity of the generated antibodies could be established. These results pave the way for the development of novel highly sensitive immunoassays selective of one or two of these Alternaria mycotoxins.

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Section: Hapten Design and Synthesismentioning

confidence: 99%

Assessment of the Optimum Linker Tethering Site of Alternariol Haptens for Antibody Generation and Immunoassay Development

Addante-Moya

Abad‐Somovilla

Abad‐Fuentes

et al. 2021

Toxins

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“…The spin system of H 2 -9/H-10/H 2 -11/H 2 -12/H 3 -13 in the 1 H- 1 H COSY spectrum ( Figure 2 ) as well as the HMBC correlations ( Figure 2 ) from H 2 -9 to C-3 and C-4 showed that the side chain was substituted at C-3. By comparing the specific rotation of 11 [[α]−21.5 (с 0.06, MeOH)] with (−)-citreoisocoumarin [[α] −29.8 ( с 0.34, MeOH)] ( Mallampudi et al, 2020 ), the 10 R configuration at C-10 in 11 was indicated. Thus, the gross structure of 11 was defined as shown.…”

Section: Resultsmentioning

confidence: 99%

Metabolites With Cytotoxic Activities From the Mangrove Endophytic Fungus Fusarium sp. 2ST2

et al. 2022

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Two new 3-decalinoyltetramic acid derivatives with peroxide bridge fusarisetins E (1) and F (2), one new chromone fusarimone A (5), two new benzofurans fusarifurans A (9) and B (10), three new isocoumarins fusarimarins A–C (11–13), as well as five known analogues 3, 4, 6–8 and 14 were isolated from mangrove endophytic fungus Fusarium sp. 2ST2. Their structures and absolute configurations were established by spectroscopic analysis, density functional theory-gauge invariant atomic orbital NMR calculation with DP4+ statistical analysis, and electronic circular dichroism calculation. Compounds 1 and 2 showed significant cytotoxicity against human A549 cell lines with IC50 values of 8.7 and 4.3 μM, respectively.

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“…Recently, this methodology was reinvestigated by the same research group [44] in the context of total synthesis of other isocoumarin core containing natural product such as 6-O-Methyl-Citreoisocoumarin, which could be further served as an important key intermediate for the total synthesis of (À )-Citreoisocoumarin, (À )-Citreoisocoumarinol, 12-epi-(À )-Citreoisocoumarinol, (À )-Mucorisocoumar in A and (À )-Mucorisocoumarin B through simple synthetic manipulations (Scheme 23).…”

Section: Carbonyl Participation Of 22-dimethyl Benzo [D]-[13]dioxinmentioning

confidence: 99%

An Overview of Water‐Mediated Alkyne Functionalization by Neighboring Group Participation of Carbonyl Groups

Pradhan

Park

2020

Adv Synth Catal

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Reviewed herein, the progress employing the assistance of a neighboring carbonyl group for alkyne functionalization reactions that are mediated by water. Proper arrangement of these transformations is synthetically worthwhile because it will allow chemists to design straightforward synthetic routes for the construction of complex architectures with perfect regio-and chemoselectivity. Researchers must understand the mechanism before aiming a new idea based on these types of transformations as they proceed through a different way in comparison to the strategies that employ carbonyl groups as a directing group for CÀ H functionalization reactions. In general, an oxygen transposition event occurs in the presence of an alkyne activator. In an aim to expose the molecular diversity that can now be accessed employing intramolecular carbonyl assistance, all the precedents are organized systematically for the first time and can be expected to serve as a comprehensive reference work. Therefore, the key arrangement of this review is schemes accompanied by a concise explanatory text describing both advantages and limitations along with the mechanism. Different transformations are ordered in sections according to the chemical structure of the assisted groups. The overall objective of this review is to promote the application of carbonyl-assisted reactions beyond the methodologies dedicated to the regioselective synthesis of carbonyl derivatives and hence, serving it as a valuable reaction archetype in modern-day research for the synthesis of carbo-and heterocycles.

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Total Synthesis of (−)-Citreoisocoumarin, (−)-Citreoisocoumarinol, (−)-12-epi-Citreoisocoumarinol, and (−)-Mucorisocoumarins A and B Using a Gold(I)-Catalyzed Cyclization Strategy

Cited by 16 publications

References 56 publications

Assessment of the Optimum Linker Tethering Site of Alternariol Haptens for Antibody Generation and Immunoassay Development

Assessment of the Optimum Linker Tethering Site of Alternariol Haptens for Antibody Generation and Immunoassay Development

Metabolites With Cytotoxic Activities From the Mangrove Endophytic Fungus Fusarium sp. 2ST2

An Overview of Water‐Mediated Alkyne Functionalization by Neighboring Group Participation of Carbonyl Groups

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