Progress in the total synthesis of epoxyquinone natural products: An update

Mehta, Goverdhan; Sengupta, Saumitra

doi:10.1016/j.tet.2017.09.030

Cited by 30 publications

(16 citation statements)

References 206 publications

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“…Epoxyquinone natural products (NPs) such as (+)-ambuic acid ( 1 ), (−)-jesterone ( 2 ), and (−)-cycloepoxydon ( 3 ) (Figure ) display promising biological activities and have attracted interest because of their structural novelty. (+)-Ambuic acid, which shows antimicrobial activity, and (−)-jesterone, possessing antimycotic activity, were isolated from the fungus Pestalotiopsis spp.…”

Section: Introductionmentioning

confidence: 99%

Total Synthesis and Structure Revision of (−)-Avicennone C

et al. 2020

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All four possible stereoisomers of the natural product (−)-avicennone C were synthesized using two different methods for ring closure. The absolute stereochemistry was elucidated unambiguously by comparison of the analytical data with those of the reported natural product and by single X-ray crystal diffraction of synthetic intermediates. The proposed structure needed to be revised with regard to the absolute configuration of the stereogenic center bearing the secondary hydroxyl group. The reported synthesis offers a flexible, selective, and efficient access to all possible stereoisomers and may be of value for the stereoselective synthesis of other epoxyquinone natural products.

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Section: Introductionmentioning

confidence: 99%

Total Synthesis and Structure Revision of (−)-Avicennone C

et al. 2020

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“…[10] The anhydrogabosines and their derivatives have attracted much synthetic attention due to their structural diversity and their wide ranging biological activity, and considerable elegant routes have been devised towards their synthesis. [1,2,11] In general, anhydrogabosines were synthesized mainly starting from benzoquinone and cyclohexenone derivatives, [10,12] as well as and the subsequent oxirane ring closure are employed as the key steps in both approaches, by which (+)-epoxydon, (-)-phyllostine, (-)-RKTS 33, and (-)-parasitenone were synthesized from δ-d-gluconolactone. iodobenzene.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of (+)‐Epoxydon, (–)‐Phyllostine, (–)‐RKTS 33, and (–)‐Parasitenone Featuring Selective Sulfonylation and Oxirane Ring Closure of Aldol Cyclization Products

et al. 2020

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Two new synthetic approaches to anhydrogabosines are developed from the polyoxygenated aldol cyclization intermediates, bearing different O‐protecting groups, which were transformed to various gabosine‐type cyclitols. Selective sulfonylation on the required hydroxyl group of the intermediates and the subsequent oxirane ring closure are employed as the key steps in both approaches, by which (+)‐epoxydon, (–)‐phyllostine, (–)‐RKTS 33, and (–)‐parasitenone were synthesized from δ‐d‐gluconolactone.

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“…Scheme 8 Catalyzed domino photooxygenation The importance of functionalized epoxyquinol frameworks in natural products served to challenge synthetic organic chemists. 24 Previous reports have shown that phenols were interesting substrates to get access to epoxyquinols through a 1 O 2 -mediated dearomatization/reduction/epoxidation sequence (Schemes 2 and 3). Nevertheless, the reduction/oxidation tactic lowers the synthetic appeal of this strategy.…”

Section: Scheme 6 Oxidative Dearomatization Towards the Synthesis Of mentioning

confidence: 99%

Visible-Light-Driven Transformations of Phenols via Energy Transfer Catalysis

Fischer

Nun²,

Coeffard³

2020

Synthesis

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In the past decade, the field of visible-light-mediated photocatalysis has been particularly thriving by offering innovative synthetic tools for the construction of functionalized architectures from simple and readily available substrates. One strategy that has been of interest is energy transfer catalysis, which is a powerful way of activating a substrate or an intermediate by using the combination of light and a relevant photosensitizer. This review deals with recent advances in energy transfer catalysis applied to phenols, which are ubiquitous in chemistry both as starting materials and as high-added-value products. Processes involving energy transfer from the excited photosensitizer to ground state oxygen and to phenol-containing substrates will be described.1 Introduction2 Intermolecular Processes2.1 Reactions with Singlet Oxygen2.2 [2+2] Cycloadditions3 Intramolecular Transformations4 Conclusions and Outlook

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Progress in the total synthesis of epoxyquinone natural products: An update

Cited by 30 publications

References 206 publications

Total Synthesis and Structure Revision of (−)-Avicennone C

Total Synthesis and Structure Revision of (−)-Avicennone C

Synthesis of (+)‐Epoxydon, (–)‐Phyllostine, (–)‐RKTS 33, and (–)‐Parasitenone Featuring Selective Sulfonylation and Oxirane Ring Closure of Aldol Cyclization Products

Visible-Light-Driven Transformations of Phenols via Energy Transfer Catalysis

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