Total Synthesis of (−)-α-Kainic acid via Chirality Transfer through Ireland–Claisen Rearrangement

Reddy, Naredla Kesava; Chandrasekhar, Srivari

doi:10.1021/jo400001t

Cited by 29 publications

(2 citation statements)

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“…New approaches, based on the formation of C3–C4 bond and involving the Ireland-Claisen rearrangement of allylic esters, were used by Indian and Japanese groups. Reddy and Chandraseker [ 21 ] utilized this rearrangement along with the Sharpless asymmetric epoxidation. The first of these reactions was used to create C3 and C4 cis stereocenters, while the Sharpless oxidation allowed the designing of chirality at C2.…”

Section: Kainic Acid and Related Metabolitesmentioning

confidence: 99%

Marine Excitatory Amino Acids: Structure, Properties, Biosynthesis and Recent Approaches to Their Syntheses

Stonik

Стоник

2020

Molecules

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This review considers the results of recent studies on marine excitatory amino acids, including kainic acid, domoic acid, dysiherbaine, and neodysiherbaine A, known as potent agonists of one of subtypes of glutamate receptors, the so-called kainate receptors. Novel information, particularly concerning biosynthesis, environmental roles, biological action, and syntheses of these marine metabolites, obtained mainly in last 10–15 years, is summarized. The goal of the review was not only to discuss recently obtained data, but also to provide a brief introduction to the field of marine excitatory amino acid research.

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Section: Kainic Acid and Related Metabolitesmentioning

confidence: 99%

Marine Excitatory Amino Acids: Structure, Properties, Biosynthesis and Recent Approaches to Their Syntheses

Stonik

Стоник

2020

Molecules

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“…One category contains true pericyclic reactions, involving a concerted flow of electrons that results in the breaking of a σ bond, simultaneous rearrangement of a π system, and formation of a new σ bond [1]. These rearrangements are effected thermally or through Lewis acid catalysis, and many landmark reactions (Cope [2], Claisen [3], Ireland-Claisen [4][5][6][7], Mislow-Evans [8], etc.) fall into this category.…”

Section: Introductionmentioning

confidence: 99%

A Formal Rearrangement of Allylic Silanols

2021

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We show that 1M aqueous HCl/THF or NaBH4/DMF allows for demercurative ring-opening of cyclic organomercurial synthons into secondary silanol products bearing terminal alkenes. We had previously demonstrated that primary allylic silanols are readily transformed into cyclic organomercurials using Hg(OTf)2/NaHCO3 in THF. Overall, this amounts to a facile two-step protocol for the rearrangement of primary allylic silanol substrates. Computational investigations suggest that this rearrangement is under thermodynamic control and that the di-tert-butylsilanol protecting group is essential for product selectivity.

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Squamostolide

2019

Retrosynthetic Analysis and Synthesis of Natural Products 1

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Total Synthesis of (−)-α-Kainic acid via Chirality Transfer through Ireland–Claisen Rearrangement

Abstract: The total synthesis of (-)-α-Kainic acid is accomplished using a linear strategy involving Noyori asymmetric reduction and chirality transfer through Ireland-Claisen rearrangement as key steps.

Cited by 29 publications

References 45 publications

Marine Excitatory Amino Acids: Structure, Properties, Biosynthesis and Recent Approaches to Their Syntheses

Marine Excitatory Amino Acids: Structure, Properties, Biosynthesis and Recent Approaches to Their Syntheses

A Formal Rearrangement of Allylic Silanols

Squamostolide

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