A Formal Total Synthesis of Dysiherbaine and Neodysiherbaine A

Lee, Hee‐Yoon; Lee, Sang‐Shin; Kim, Hoon Seok; Lee, Kang Mun

doi:10.1002/ejoc.201200439

Cited by 14 publications

(3 citation statements)

References 48 publications

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“…Mild reduction of the aldehyde group in FF is a path to important furanic building blocks furfuryl alcohol (FA) and furfuryl amine (FAM), which are widely used for the development of functional or dynamic molecular and biomolecular systems. Examples of possible areas of applications include but are not limited to the synthesis of biologically active compounds [ 87 , 88 , 89 , 90 ], oxanorbornane-based amphiphiles [ 91 , 92 , 93 , 94 ], supramolecular systems [ 95 ], self-assemblies [ 96 ], self-healing polymers and other dynamic systems [ 28 ].…”

Section: Selectivity Of Diels-alder Cycloaddition With Furfural Derivatives As Substratesmentioning

confidence: 99%

Intermolecular Diels-Alder Cycloadditions of Furfural-Based Chemicals from Renewable Resources: A Focus on the Regio- and Diastereoselectivity in the Reaction with Alkenes

Galkin

Ananikov

2021

IJMS

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A recent strong trend toward green and sustainable chemistry has promoted the intensive use of renewable carbon sources for the production of polymers, biofuels, chemicals, monomers and other valuable products. The Diels-Alder reaction is of great importance in the chemistry of renewable resources and provides an atom-economic pathway for fine chemical synthesis and for the production of materials. The biobased furans furfural and 5-(hydroxymethyl)furfural, which can be easily obtained from the carbohydrate part of plant biomass, were recognized as “platform chemicals” that will help to replace the existing oil-based refining to biorefining. Diels-Alder cycloaddition of furanic dienes with various dienophiles represents the ideal example of a “green” process characterized by a 100% atom economy and a reasonable E-factor. In this review, we first summarize the literature data on the regio- and diastereoselectivity of intermolecular Diels-Alder reactions of furfural derivatives with alkenes with the aim of establishing the current progress in the efficient production of practically important low-molecular-weight products. The information provided here will be useful and relevant to scientists in many fields, including medical and pharmaceutical research, polymer development and materials science.

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Section: Selectivity Of Diels-alder Cycloaddition With Furfural Derivatives As Substratesmentioning

confidence: 99%

Intermolecular Diels-Alder Cycloadditions of Furfural-Based Chemicals from Renewable Resources: A Focus on the Regio- and Diastereoselectivity in the Reaction with Alkenes

Galkin

Ananikov

2021

IJMS

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“…In 2012, Lee et al described the preparation of functionalized pyranofuran 139, an intermediate in the synthesis of dysiherbaine and neodysiherbaine A [124]. A domino olefin methatesis reaction of 1-alkyl-3-(allyloxy)-7-oxabicyclo[2.2.1]hept-5-ene 137 produced the fused bis(oxacyclic) structure 138 with complete control of the relative stereochemistry at the quaternary carbon centre and the ring junction of the dysiherbaine core skeleton (Scheme 40).…”

Section: The Sequence Rom-ring-closing Metathesis (Rcm): Ring Rearranmentioning

confidence: 99%

Ring Rearrangement Metathesis in 7-Oxabicyclo[2.2.1]heptene (7-Oxanorbornene) Derivatives. Some Applications in Natural Product Chemistry

Roscales

Plumet

2017

Natural Product Communications

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Metathesis reactions is firmly established as a valuable synthetic tool in organic chemistry, clearly comparable with the venerable Diels-Alder and Wittig reactions and, more recently, with the metal-catalyzed cross-coupling reactions. Metathesis reactions can be considered as a fascinating synthetic methodology, allowing different variants regarding substrate (alkene and alkyne metathesis) and type of metathetical reactions. On the other hand, tandem metathesis reactions such Ring Rearrangement Metathesis (RRM) and the coupling of metathesis reaction with other reactions of alkenes such as Diels-Alder or Heck reactions, makes metathesis one of the most powerful and reliable synthetic procedure. In particular, Ring-Rearrangement Metathesis (RRM) refers to the combination of several metathesis transformations into a domino process such as ringopening metathesis (ROM)/ring-closing metathesis (RCM) and ROM-cross metathesis (CM) in a one-pot operation. RRM delivers complex frameworks that are difficult to assemble by conventional methods constitutingan atom economic process. RRM is applicable to mono-and polycyclic systems of varying ring sizes such as cyclopropene, cyclobutene, cyclopentene, cyclohexene, pyran systems, bicyclo[2.2.1]heptene derivatives, bicyclo[2.2.2]octene derivatives, bicyclo[3.2.1]octene derivatives and bicyclo[3.2.1]octene derivatives. In this review our attention has focused on the RRM reactions in 7-oxabicyclo[2.2.1]heptene derivatives and on their application in the synthesis of natural products or significant subunits of them.

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“…Neodysiherbaine A ( 14 ) is a neurologically active compound that acts as a glutamate receptor agonist and shows epileptogenic properties. Contiguous to the isolation, the first synthesis has been carried out by the same research group [42] and several other syntheses followed [43–47]. …”

Section: Reviewmentioning

confidence: 99%

The direct oxidative diene cyclization and related reactions in natural product synthesis

Adrian¹,

Gross²,

Stark³

2016

Beilstein J. Org. Chem.

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SummaryThe direct oxidative cyclization of 1,5-dienes is a valuable synthetic method for the (dia)stereoselective preparation of substituted tetrahydrofurans. Closely related reactions start from 5,6-dihydroxy or 5-hydroxyalkenes to generate similar products in a mechanistically analogous manner. After a brief overview on the history of this group of transformations and a survey on mechanistic and stereochemical aspects, this review article provides a summary on applications in natural product synthesis. Moreover, current limitations and future directions in this area of chemistry are discussed.

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A Formal Total Synthesis of Dysiherbaine and Neodysiherbaine A

Cited by 14 publications

References 48 publications

Intermolecular Diels-Alder Cycloadditions of Furfural-Based Chemicals from Renewable Resources: A Focus on the Regio- and Diastereoselectivity in the Reaction with Alkenes

Intermolecular Diels-Alder Cycloadditions of Furfural-Based Chemicals from Renewable Resources: A Focus on the Regio- and Diastereoselectivity in the Reaction with Alkenes

Ring Rearrangement Metathesis in 7-Oxabicyclo[2.2.1]heptene (7-Oxanorbornene) Derivatives. Some Applications in Natural Product Chemistry

The direct oxidative diene cyclization and related reactions in natural product synthesis

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