Catalytic Asymmetric Synthesis of Isochroman Derivatives

Tamanna,; Kumar, Mukesh; Joshi, Kavita; Chauhan, Pankaj

doi:10.1002/adsc.202000243

Cited by 21 publications

(8 citation statements)

References 71 publications

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“…The efficacy of the synthesis of hexahydroisochromen-6-ones was further demonstrated through transformation to different functionalities. The hexahydroisochromen-6-ones were investigated under oxidative aromatization to form isochromanols, which are also present as a key core of many biologically active natural products . Pd(OAc) 2 was employed as a catalyst in the presence of a catalytic amount of 4-dimethylaminopyridine (DMAP) and TsOH under an oxygen atmosphere for the aromatization of hexahydroisochromen-6-ones to isochromanols in dimethyl sulfoxide (DMSO) with good yields (details are provided in the Experimental Section).…”

Section: Resultsmentioning

confidence: 99%

Stereoselective Synthesis of Oxacycles via Ruthenium-Catalyzed Atom-Economic Coupling of Propargyl Alcohols and Michael Acceptors

2021

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Synthesis of β-hydroxyenones and its application toward development of tetrahydro-4H-pyran-4-one in an atom-economic fashion is limited. This manuscript describes a ruthenium-catalyzed atom-economic coupling of pent-2yne-1,5-diols and Michael acceptors as an efficient route for the synthesis of βhydroxyenones with excellent yields and high regioselectivity. The β-hydroxyenones further undergo a 6-endo trig cyclization under acid-catalyzed conditions to deliver the tetrahydro-4H-pyran-4-ones with high diastereoselectivity. An intramolecular aldol condensation under mild basic conditions and palladium-catalyzed oxidative aromatization was developed for the synthesis of hexahydro-6H-isochromen-6-ones and isochromanols, respectively, from highly substituted tetrahydro-4H-pyran-4-ones with excellent yield and diastereoselectivity. Overall, this work demonstrates the synthetic potential toward the synthesis of oxacycles like tetrahydro-4H-pyran-4-ones, hexahydro-6H-isochromen-6-ones, and isochromanols via an atom-economic catalysis.

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Section: Resultsmentioning

confidence: 99%

Stereoselective Synthesis of Oxacycles via Ruthenium-Catalyzed Atom-Economic Coupling of Propargyl Alcohols and Michael Acceptors

2021

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“…To date, very few methods exist to construct isochromans stereoselectively [15–17] . Asymmetric variants of the oxa‐Pictet–Spengler reaction have achieved high levels of enantioselectivity at the isochroman C3 [18, 19] .…”

Section: Figurementioning

confidence: 99%

Divergent Asymmetric Synthesis of Panowamycins, TM‐135, and Veramycin F Using C−H Insertion with Donor/Donor Carbenes

et al. 2022

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Panowamycins are a group of isochromanbased natural products first isolated from Streptomyces sp. K07-0010 in 2012 by Satoshi Ōmura and co-workers that exhibit modest anti-trypanosomal activity. Herein we demonstrate the first syntheses of these natural products and their epimers. Stereoselective dirhodiumcatalyzed CÀ H insertion reactions with a donor/donor carbene construct the substituted isochroman core in the key bond-forming step. The syntheses are completed without the use of protecting groups and feature a latestage Wacker oxidation. Incongruent NMR spectra between natural and synthetic samples revealed the structural misassignment of panowamycin A and veramycin F. Computational NMR studies suggested panowamycin A to be an alternate diastereomer, which was confirmed by synthesizing this isomer. Concurrent with this work, in 2021 Mahmud and co-workers came to the same conclusion with an updated NMR analysis of panowamycin A. In a divergent, asymmetric sequence, we report the synthesis of panowamycin A, panowamycin B, TM-135, and veramycin F.

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“…Due to a broad spectrum of biological activities and potential applications as drugs and key intermediates in organic synthesis, the stereoselective synthesis of isochroman scaffolds is very important. In this context, a handful of transition-metal-catalyzed and organocatalyzed stereoselective transformations have been published in the past decade . Recently, ortho -formyl homochalcones were utilized as suitable substrates for organocatalyzed domino 1,2-addition/oxa-Michael reactions to afford isochromans bearing two stereogenic centers (Scheme a) …”

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confidence: 99%

Asymmetric Synthesis of Cyclohexenone-Fused Isochromans via Quinidine-Catalyzed Domino Peroxyhemiacetalization/Oxa-Michael Addition/Desymmetrization Sequence

et al. 2022

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A highly enantio- and diastereoselective synthesis of highly functionalized isochromans was achieved through an organocatalyzed domino reaction. Quinidine as the catalyst initiates a peroxyhemiacetalization/oxa-Michael/desymmetrization domino sequence between various 2,5-cyclohexadienone-tethered aryl aldehydes with hydroperoxides to generate the single diastereomers of isochromans appended with a cyclohexenone ring bearing three vicinal stereocenters in good yields and high enantioselectivities under ambient reaction conditions.

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Catalytic Asymmetric Synthesis of Isochroman Derivatives

Cited by 21 publications

References 71 publications

Stereoselective Synthesis of Oxacycles via Ruthenium-Catalyzed Atom-Economic Coupling of Propargyl Alcohols and Michael Acceptors

Stereoselective Synthesis of Oxacycles via Ruthenium-Catalyzed Atom-Economic Coupling of Propargyl Alcohols and Michael Acceptors

Divergent Asymmetric Synthesis of Panowamycins, TM‐135, and Veramycin F Using C−H Insertion with Donor/Donor Carbenes

Asymmetric Synthesis of Cyclohexenone-Fused Isochromans via Quinidine-Catalyzed Domino Peroxyhemiacetalization/Oxa-Michael Addition/Desymmetrization Sequence

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