Total synthesis of glycinoeclepin A

Murai, Akio; Tánimoto, Norihiko; Sakamoto, Noriko; Masamune, Tadashi

doi:10.1021/ja00214a064

Cited by 82 publications

(39 citation statements)

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“…Hence, the addition of activators has been suggested [191]. These "activators" (most often α,β-unsaturated alcohols, ketones, or nitriles) seem to act as suicide substrates for several oxidoreductases [192,193], whereas, for the reduction of cyclopentanoid 1,3-diketones, stereoselectivity was high, and most often [194] low selectivity was observed for cyclohexanoid 1,3-diketones [184,[194][195][196][197].…”

Section: Figure 2110mentioning

confidence: 99%

Yeast‐Mediated Stereoselective Synthesis

Csük

2016

Green Biocatalysis

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Section: Figure 2110mentioning

confidence: 99%

Yeast‐Mediated Stereoselective Synthesis

Csük

2016

Green Biocatalysis

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“…The resulting enolate was converted to triflate 120. 62 A convergent synthesis of tetracyclic steroid skeleton 123 has been reported by Deslongchamps, which involved consecutive base-induced Michael addition of allyl b-keto ester (bicyclic Nazarov reagent) 122 to cyclohexenone 121 and palladium-catalyzed decarboxylation in the presence of morpholine 63 (Scheme 32).…”

Section: Synthesis Of A-methylene Carbonyl Compounds By Deacetox-mentioning

confidence: 99%

Dawn of organopalladium chemistry in the early 1960s and a retrospective overview of the research on palladium-catalyzed reactions

Tsuji

2015

Tetrahedron

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“…Only the allyl ester in 100 was cleaved selectively to give the ketone, which was converted to trflate 101 without attacking the methyl ester and acetate in 100. 23) Shimizu and coworkers reported an interesting synthetic method of α-keto carboxylic acids such as 105. The diallyl 2-oxosuccinate 104 was prepared from diallyl oxalate (102) and allyl 3-phenylpropionate (103), and chemoselective decarboxylation of only the allyl β-keto carboxylate in 104 took place to give the α-keto carboxylic acid 105.…”

Section: )19)mentioning

confidence: 99%

Development of .BETA.-keto ester and malonate chemistry Palladium-catalyzed new reactions of their allylic esters

Tsuji

2004

Proceedings of the Japan Academy. Ser. B: Physical and Biologic

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Introduction.Palladium is now regarded as the most versatile metal among a number of transition metals used for organic synthesis.1) We started research on organopalladium chemistry in early 1960s, and discovered carbon-carbon bond formation by using palladium complexes for the first time. Since then we have carried out extensive studies on organopalladium. One topic of these studies is palladium-catalyzed reaction of allylic compounds via π-allylpalladium complexes. Among a number of new catalytic reactions discovered in this area, synthetically useful catalytic reactions of allyl β-keto carboxylates and malonates via palladium enolates are summarized in this review. The first palladium-mediated carbon-carbon bond formation. At first we investigated the possibility of carbon-carbon bond formation by using palladium complexes. When we treated the stable PdCl 2 complex of cyclooctadiene (COD) 1 with diethyl malonate in ether in the presence of sodium carbonate at room temperature, a facile carbopalladation occurred to give the new stable complex 2. This reaction is the first example of carbopalladation of an alkene in palladium chemistry, resulting in the carbon-carbon bond formation. The palladium-carbon σ-bond in the complex 2 is stabilized by coordination of π-olefin bond. By the treatment of the complex 2 with a base, malonate anion was generated and attacked the palladium-carbon bond, affording the bicyclo[6. Abstract: During extensive studies on π-allylpalladium chemistry, we have developed classical β-keto ester and malonate chemistry to a new generation by discovering a variety of palladium-catalyzed reactions of their allylic esters. Palladium enolates are generated from allyl β-keto esters after decarboxylation and undergo the following transformations; a) reductive elimination to provide α-allyl ketones, b) elimination of β-hydrogen to give α, β-unsaturated ketones, c) formation of α-methylene ketones, d) hydrogenolysis to give ketones, e) aldol condensation, and f) Michael addition. Allyl malonates and cyanoacetes undergo similar reactions. Results of these studies, including several applications carried out by other researchers are summarized.

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Total synthesis of glycinoeclepin A

Cited by 82 publications

References 1 publication

Yeast‐Mediated Stereoselective Synthesis

Yeast‐Mediated Stereoselective Synthesis

Dawn of organopalladium chemistry in the early 1960s and a retrospective overview of the research on palladium-catalyzed reactions

Development of .BETA.-keto ester and malonate chemistry Palladium-catalyzed new reactions of their allylic esters

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