Total Synthesis of Neoaltenuene

Altemöller, Martina; Podlech, Joachim

doi:10.1002/ejoc.200900125

Cited by 24 publications

(17 citation statements)

References 56 publications

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“…[8][9][10]15] The key reaction would be a Suzuki reaction of a suitably substituted aryl boronate with a highly oxygenated aryl bromide, allowing C-C bond formation and generation of the typical lactone moiety of these metabolites in a single step. [8][9][10]15] The key reaction would be a Suzuki reaction of a suitably substituted aryl boronate with a highly oxygenated aryl bromide, allowing C-C bond formation and generation of the typical lactone moiety of these metabolites in a single step.…”

Section: Resultsmentioning

confidence: 99%

“…[2,3] Although the toxicity of these mycotoxins is lower than that of others (e.g., aflatoxins), [4] infestation with Alternaria spp. [5] Total syntheses of these compounds [6,7] and of the structurally related toxins altenuene, isoaltenuene, [8] neoaltenuene, [9] and alterlactone have been reported. [5] Total syntheses of these compounds [6,7] and of the structurally related toxins altenuene, isoaltenuene, [8] neoaltenuene, [9] and alterlactone have been reported.…”

Section: Introductionmentioning

confidence: 99%

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Revision of the Structure and Total Synthesis of Altenuisol

2012

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A total synthesis of the reported structure of altenuisol is described. Comparison of the 1H NMR spectra of the synthesized compound and of the natural product revealed that the originally proposed structure was not correct. Consequently, two constitutional isomers were synthesized. The spectra of one of these compounds – a structure originally proposed as the structure of altertenuol – matched perfectly with the spectra of the natural product. The total synthesis of altenuisol was thus achieved starting with phloroglucinic acid and protocatechuic aldehyde in 10 steps and in 23 % yield, where the longest linear sequence consisted of 6 steps. The key step was a Suzuki coupling with concomitant formation of the lactone ring. Whether altertenuol is identical with altenuisol could not be decided.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Revision of the Structure and Total Synthesis of Altenuisol

2012

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“…Chemical syntheses have been achieved for a few bioactive dibenzo-α-pyrones such as altenuene (1) [94], isoaltenuene (2) [94], neoaltenuene (5) [95], alternariol (10) [96], alternariol 9-methyl ether (11) [96], altertenuol (15) [97], dehydroaltenusin (17) [98], graphislactones A (18), C (20), D (21) and H (25) [99], TMC-264 (28) [90], lysilactone A (34) [5], urolithins A-C (40, 42 and 43) [100], and urolithin M-7 (48) [101]. In addition, some dibenzo-α-pyrones are the important precursors of many synthetic drugs [14][15][16][17][18].…”

Section: Conclusion and Future Perspectivesmentioning

confidence: 99%

Natural Dibenzo-α-Pyrones and Their Bioactivities

Mao

Sun

et al. 2014

Molecules

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Natural dibenzo-α-pyrones are an important group of metabolites derived from fungi, mycobionts, plants and animal feces. They exhibit a variety of biological activities such as toxicity on human and animals, phytotoxicity as well as cytotoxic, antioxidant, antiallergic, antimicrobial, antinematodal, and acetylcholinesterase inhibitory properties. Dibenzo-α-pyrones are biosynthesized via the polyketide pathway in microorganisms or metabolized from plant-derived ellagitannins and ellagic acid by intestinal bacteria. At least 53 dibenzo-α-pyrones have been reported in the past few decades. This mini-review aims to briefly summarize the occurrence, biosynthesis, biotransformation, as well as their biological activities and functions. Some considerations related to synthesis, production and applications of dibenzo-α-pyrones are also discussed.

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“…We noted scattered reports in the literature describing the addition of organometallic nucleophiles to cyclohexanones bearing unprotected β-hydroxyl groups that provided 1,3- syn -diols with high diastereoselectivity. 14 In those cases, however, the hydroxyl groups were fixed in an axial position. In at least one case, 14d an isomeric equatorial alcohol gave the opposite facial selectivity.…”

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confidence: 99%

“…14 In those cases, however, the hydroxyl groups were fixed in an axial position. In at least one case, 14d an isomeric equatorial alcohol gave the opposite facial selectivity. Hence enone 7 would presumably need to adopt an all axial conformation to exhibit high diastereoselectivity.…”

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confidence: 99%