An Unprecedented Synthesis of 3,3‐Disubstituted Isochroman‐1,4‐diones Using Nitrones as Oxygen Atom Donors

Sathi, Vidya; Deepthi, Ani; Thomas, Noble V.

doi:10.1002/jhet.3619

Cited by 5 publications

(2 citation statements)

References 32 publications

(27 reference statements)

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“…Here we propose the mechanism for DuxM as an initial Baeyer–Villiger oxidation of 8a . This type of reaction on triketones has literature precedent, , and the following steps are interpreted from the known characteristics of DuxM. The mechanism allows the formation of lamellicolic anhydride via an interesting decarboxylative dehydration.…”

Section: Resultsmentioning

confidence: 99%

Talauxins: Hybrid Phenalenone Dimers from Talaromyces stipitatus

Chaudhary

Crombie²,

Vuong³

et al. 2020

J. Nat. Prod.

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Cultivation and extraction of the fungus Talaromyces stipitatus led to the isolation of five new oxyphenalenone–amino acid hybrids, which were named talauxins E, Q, V, L, and I based on the corresponding one-letter amino acid codes, along with their putative biosynthetic precursor, duclauxin. The rapid reaction of duclauxin with amino acids to produce talauxins was demonstrated in vitro and exploited to generate a small library of natural and unnatural talauxins. Talauxin V was shown to undergo spontaneous elimination of methyl acetate to yield the corresponding neoclauxin scaffold. This process was modeled using density functional theory calculations, revealing a dramatic change in conformation resulting from the syn elimination of methyl acetate.

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Section: Resultsmentioning

confidence: 99%

Talauxins: Hybrid Phenalenone Dimers from Talaromyces stipitatus

Chaudhary

Crombie²,

Vuong³

et al. 2020

J. Nat. Prod.

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show abstract

“…et al described a sequential one-pot protocol to access the chromeno[2,3-b]isoindolo[1,2-e]pyrrole scaffold 136 via acid-catalyzed rearrangement. 131 At room temperature, the stirring of ninhydrin 1 and 2-aminochromen-4-ones 134 in AcOH furnished chromeno-indeno-pyrrole derivatives 135, which upon reux with aromatic amines 2 in AcOH, delivered the nal product 136 (Scheme 48).Isochroman-1,4-dionesThe synthesis of 3,3-disubstituted isochroman-1,4-dione 139 was reported by Deepthi et al involving ninhydrin 1, secondary amines 137 and N-methyl-C-phenyl nitrone 138 (Scheme 49) 132. …”

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confidence: 99%