Asymmetric synthesis of aerothionin, a marine dimeric spiroisoxazoline natural product, employing optically active spiroisoxazoline derivative

Ogamino, Takahisa; Obata, Rika; Nishiyama, Shigeru

doi:10.1016/j.tetlet.2005.11.097

Cited by 44 publications

(23 citation statements)

References 29 publications

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“…The zinc mediated chelate controlled intramolecular hydride delivery20 favored the trans isomer 19 over cis isomer 20 . The relative configurations of diastereomers 19 and 20 were assigned using 1 H and 13 C NMR which were consistent with literature data16a Accomplishing the synthesis of the known spiroisoxazoline ketone 9 and alcohol 19 also facilitated the formal syntheses of aerophobin‐1,16b aerothionin,16a homoaerothionin,16k aeroplysinin‐1,21 (±)‐purealin A,22 calafianin,23 subereamollines A and B16e through previously developed routes.…”

Section: Resultssupporting

confidence: 80%

Doubling the Capacity of Lithium Manganese Oxide Spinel by a Flexible Skinny Graphitic Layer

et al. 2014

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By coating nanoparticular lithium manganese oxide (LMO) spinel with a few layers of graphitic basal planes, the capacity of the material reached up to 220 mA h g−1 at a cutoff voltage of 2.5 V. The graphitic layers 1) provided a facile electron‐transfer highway without hindering ion access and, more interestingly, 2) stabilized the structural distortion at the 3 V region reaction. The gain was won by a simple method in which microsized LMO was ball‐milled in the presence of graphite with high energy. Vibratory ball milling pulverized the LMO into the nanoscale, exfoliated graphite of less than 10 layers and combined them together with an extremely intimate contact. Ab initio calculations show that the intrinsically very low electrical conductivity of the tetragonal phase of the LMO is responsible for the poor electrochemical performance in the 3 V region and could be overcome by the graphitic skin strategy proposed.

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Section: Resultssupporting

confidence: 80%

Doubling the Capacity of Lithium Manganese Oxide Spinel by a Flexible Skinny Graphitic Layer

et al. 2014

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“…Similar electrochemical protocols were also utilized in the total syntheses of aeroplysinin (89) and aerothionin (90) (Scheme 16). 158,159 In these cases, electrochemical oxi-dation of oxime 86 under constant potential conditions provided racemic spirocyclic isoxazoline 87 in 68% yield. It was shown that the methoxycarbonyl group was essential for obtaining satisfactory yields (the yield when R = H was only 28%).…”

Section: Spirocyclesmentioning

confidence: 99%

“…Further saponification and decarboxylation then furnished enantiopure aeroplysinins 89. 158 Additionally, condensation of alcohols (-)-88 and (+)-88 with 1,4-diaminobutane yielded optically pure aerothionins (90) in 33% and 28% yield, respectively. 158…”

Section: Spirocyclesmentioning

confidence: 99%

Anodic Oxidation as an Enabling Tool for the Synthesis of Natural Products

Geske

Sato²,

Opatz³

2020

Synthesis

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Electrochemistry provides a valuable toolbox for organic synthesis and offers an appealing, environmentally benign alternative to the use of stoichiometric quantities of chemical oxidants or reductants. Its potential to control current efficiency along with providing alternative reaction conditions in a classical sense makes electrochemistry a suitable method for large-scale industrial transformations as well as for laboratory applications in the synthesis of complex molecular architectures. Even though research in this field has intensified over the recent decades, many synthetic chemists still hesitate to add electroorganic reactions to their standard repertoire, and hence, the full potential of preparative organic electrochemistry has not yet been unleashed. This short review highlights the versatility of anodic transformations by summarizing their application in natural product synthesis.1 Introduction2 Shono-Type Oxidation3 C–N/N–N Bond Formation4 Aryl–Alkene/Aryl–Aryl Coupling5 Cycloadditions Triggered by Oxidation of Electron-Rich Arenes6 Spirocycles7 Miscellaneous Transformations8 Future Prospects

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“…653 Alternatively, incorporation of a pending nucleophile into the phenol unit allows the design of various types of intramolecular reaction manifolds for construction of spirodienone derivatives. [654][655][656][657][658][659][660][661] This feature has been leveraged in the synthesis of aeroplysinin (Scheme 85), [662][663][664][665] discorhabdin C (Scheme 86), [666][667][668][669] gymnastatin A (Scheme 87) 670 as well as heliannuol E (Scheme 88) [671][672][673] and derivatives thereof. 674 Catechols and related derivatives constitute another class of compounds that can undergo two-electron anodic oxidation to afford, for example, 1,2-benzoquinones.…”

Section: Electrochemical Oxidative Cross-couplingsmentioning

confidence: 99%

Electrochemical strategies for C–H functionalization and C–N bond formation

2018

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Conventional methods for carrying out carbon-hydrogen functionalization and carbon-nitrogen bond formation are typically conducted at elevated temperatures, and rely on expensive catalysts as well as the use of stoichiometric, and perhaps toxic, oxidants. In this regard, electrochemical synthesis has recently been recognized as a sustainable and scalable strategy for the construction of challenging carbon-carbon and carbon-heteroatom bonds. Here, electrosynthesis has proven to be an environmentally benign, highly effective and versatile platform for achieving a wide range of nonclassical bond disconnections via generation of radical intermediates under mild reaction conditions. This review provides an overview on the use of anodic electrochemical methods for expediting the development of carbon-hydrogen functionalization and carbon-nitrogen bond formation strategies. Emphasis is placed on methodology development and mechanistic insight and aims to provide inspiration for future synthetic applications in the field of electrosynthesis.

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Asymmetric synthesis of aerothionin, a marine dimeric spiroisoxazoline natural product, employing optically active spiroisoxazoline derivative

Cited by 44 publications

References 29 publications

Doubling the Capacity of Lithium Manganese Oxide Spinel by a Flexible Skinny Graphitic Layer

Doubling the Capacity of Lithium Manganese Oxide Spinel by a Flexible Skinny Graphitic Layer

Anodic Oxidation as an Enabling Tool for the Synthesis of Natural Products

Electrochemical strategies for C–H functionalization and C–N bond formation

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