Ruthenium-Catalyzed Alkyne−Propargyl Alcohol Addition. An Asymmetric Total Synthesis of (+)-α-Kainic Acid

Trost, Barry M.; Rudd, Michael T.

doi:10.1021/ol034241y

Cited by 60 publications

(22 citation statements)

References 28 publications

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“…The utility of this method was demonstrated in the total synthesis of (+)-a-kainic acid (350; Scheme 31). [239] In this case, protected aminodiyne 351 underwent regioselective cycloisomerization to unsaturated ketone 352 in high yield and with no loss of enantiopurity at the propargylic center. This intermediate could be elaborated into the neuroexcitatory natural product (+)-a-kainic acid in several steps.…”

Section: Ruthenium Catalysismentioning

confidence: 98%

Ruthenium‐Catalyzed Reactions—A Treasure Trove of Atom‐Economic Transformations

2005

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The demand for new chemicals spanning the fields of health care to materials science combined with the pressure to produce these substances in an environmentally benign fashion pose great challenges to the synthetic chemical community. The maximization of synthetic efficiency by the conversion of simple building blocks into complex targets remains a fundamental goal. In this context, ruthenium complexes catalyze a number of non-metathesis conversions and allow the rapid assembly of complex molecules with high selectivity and atom economy. These complexes often exhibit unusual reactivity. Careful consideration of the mechanistic underpinnings of the transformations can lead to the design of new reactions and the discovery of new reactivity.

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Section: Ruthenium Catalysismentioning

confidence: 98%

Ruthenium‐Catalyzed Reactions—A Treasure Trove of Atom‐Economic Transformations

2005

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“…Treatment of diynes with coordinatively unsaturated CpRu complexes generates a cyclic bis‐alkylidene ruthenacycle 10 (Scheme ) . Two resonance forms, 10 a and 10 b , the former being a bis‐alkylideneruthenium complex,provide insight into the reactivity of such a system.…”

Section: Discussionmentioning

confidence: 99%

Organic Synthesis. Use of Alkynes as a Key to Innovation in Designing Structure for Function

Trost

Tracy

2017

Israel Journal of Chemistry

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A personal perspective of one aspect of what needs to be done to fulfill the scientific objective of improving the world in which we live is presented. One specific goal of this journey is to enable the best design of molecular structure for function regardless of complexity. Meeting this objective requires improvements in the fundamental tools of constructing synthetic reactions. What is presented is just one part of our journey which started with a fundamental question; do the unique features of alkyne building blocks provide an unusual opportunity to achieve the noted objectives? The story begins with the discovery of new synthetic tools and concludes with numerous illustrations of the broad potential these tools appear to possess.

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“…Then, the resulting suspension was warmed to 0°C, and stirred for an additional 30 min. The crude product was purified by silica gel column chromatography (methanol/dichloromethane, 1:25) to give 35 ( Kainic Acid (2): Jones reagent [29] (8 n; 84 μL, 0.670 mmol) was added to a solution of methyl (2S,3S,4S)-3-(2-hydroxyethyl)-2-(hydroxymethyl)-4-(prop-1-en-2-yl)pyrrolidine-1-carboxylate (35; 16.3 mg, 0.0670 mmol) in acetone at 0°C. The mixture was extracted with ethyl acetate (3 ϫ), and the combined organic extracts were washed with saturated aqueous NH 4 Cl and brine.…”

Section: Methyl (1s3ar7as)-1-(hydroxymethyl)-4-(iodomethyl)-4-methymentioning

confidence: 99%

A Unified Strategy for Kainoid Synthesis

2014

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A unified strategy for kainoid synthesis was developed. The key features of the strategy involve a Claisen–Ireland rearrangement to construct the contiguous stereogenic centers and a palladium‐catalyzed formation of the pyrrolidine ring with complete stereoselectivity. The present protocol has enabled rapid access to a wide range of kainoids with diverse types of substituents (alkenyl, aryl, and alkyl groups) at the 4‐position of the pyrrolidine ring, starting from the common intermediate and appropriate acetic acid derivatives. To test the generality of the strategy, we have accomplished the syntheses of kainic acid, o‐methoxyphenyl derivative (MFPA), and a novel cyclopropyl derivative (CPKA), using 3‐methylbut‐3‐enoic acid, 2‐(2‐methoxyphenyl)acetic acid, and 2‐cyclopropylacetic acid, respectively.

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Ruthenium-Catalyzed Alkyne−Propargyl Alcohol Addition. An Asymmetric Total Synthesis of (+)-α-Kainic Acid

Cited by 60 publications

References 28 publications

Ruthenium‐Catalyzed Reactions—A Treasure Trove of Atom‐Economic Transformations

Ruthenium‐Catalyzed Reactions—A Treasure Trove of Atom‐Economic Transformations

Organic Synthesis. Use of Alkynes as a Key to Innovation in Designing Structure for Function

A Unified Strategy for Kainoid Synthesis

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