Enantioselective total syntheses of cedrelin A and methylated paralycolin B using Pd-catalyzed asymmetric intramolecular Friedel–Crafts allylic alkylation of phenols

Suzuki, Yuta; Matsuo, Nobuaki; Nemoto, Tetsuhiro; Hamada, Y.

doi:10.1016/j.tet.2013.05.007

Cited by 13 publications

(8 citation statements)

References 21 publications

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“…The enantioselective total synthesis of 127 and 128 was achieved in overall yields of 16.5 % and 35.2 % and 12 and 10 steps from 129 and 132 , respectively (Scheme 25). [121] …”

Section: Palladium‐catalyzed Aas Reactionsmentioning

confidence: 99%

“…[120] . [121] The application of Pd-catalyzed AAS to assemble the tricyclic indole motif was demonstrated through the first enantioselective total syntheses of (À )-agroclavine 135 (135) and (À )elymoclavine (136) (Scheme 26). [122] The number of highly enantioselective processes that produce quaternary stereocenters under mild reaction conditions is limited.…”

Section: Carbon Nucleophilesmentioning

confidence: 99%

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Applications of Transition‐Metal‐Catalyzed Asymmetric Allylic Substitution in Total Synthesis of Natural Products: An Update

Mohammadkhani

Heravi

2020

The Chemical Record

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Metal‐catalyzed asymmetric allylic substitution (AAS) reaction is one of the most synthetically useful reactions catalyzed by metal complexes for the formation of carbon‐carbon and carbon‐heteroatom bonds. It comprises the substitution of allylic substrates with a wide range of nucleophiles or SN2′‐type allylic substitution, which results in the formation of the above‐mentioned bonds with high levels of enantioselective induction. AAS reaction tolerates a broad range of functional groups, thus has been successfully applied in the asymmetric synthesis of a wide range of optically pure compounds. This reaction has been extensively used in the total synthesis of several complex molecules, especially natural products. In this review, we try to highlight the applications of metal (Pd, Ir, Mo, or Cu)‐catalyzed AAS reaction in the total synthesis of the biologically active natural products, as a key step, updating the subject from 2003 till date.

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“…The enantioselective total synthesis of 127 and 128 was achieved in overall yields of 16.5 % and 35.2 % and 12 and 10 steps from 129 and 132 , respectively (Scheme 25). [121] …”

Section: Palladium‐catalyzed Aas Reactionsmentioning

confidence: 99%

Section: Carbon Nucleophilesmentioning

confidence: 99%

Applications of Transition‐Metal‐Catalyzed Asymmetric Allylic Substitution in Total Synthesis of Natural Products: An Update

Mohammadkhani

Heravi

2020

The Chemical Record

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“…Hamada and co-workers in 2013 demonstrated the initial asymmetric total syntheses of cedrelin A and methylated paralycolin B, employing mediated enantioselective intramolecular FC allylic alkylation reaction of phenols as the main step. 153 Total synthesis of cedrelin A 138 was initiated from aldehyde 140, 154 which was transformed into allyl carbonate derivative 141 upon several steps. Next, the mediated enantioselective intramolecular FC allylic alkylation of 141 was examined.…”

Section: Applications Of Friedel–crafts In Total Synthesis Of Natural...mentioning

confidence: 99%

Applications of Friedel–Crafts reactions in total synthesis of natural products

et al. 2018

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“…[311] More recently, Hamada and co-workers described the first enantioselective synthesis of cedrelin A (332), wherein a,bunsaturated ester C77 was an intermediate. [312] This highly functionalized biphenyl derivative was synthesized in an excellent yield by the S.-M. cross-coupling reaction illustrated in entry 30 of Table 9. The key step of the total synthesis was the preparation of compound 400 by Pd(dba)2/(R,R)-L1-catalyzed asymmetric intramolecular Friedel-Crafts allylic alkylation of compound 399 which was obtained in 3 steps from C77 (Scheme 95).…”

Section: Figure 20 Structures Of Compounds 384-386mentioning

confidence: 99%

Recent Applications of Phosphane-based Palladium Catalysts in Suzuki-Miyaura Reactions Involved in Total Syntheses of Natural Products

Rossi¹,

Bellina²,

Lessi³

et al. 2015

COC

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This review with 800 references illustrates applications of Suzuki-Miyaura (S.-M.) reactions in the total syntheses of 147 natural products that were made in the period 2010–2013. The review has been organized on the basis of the seven classes of phosphane-based Pd catalysts that have been used in the reported total syntheses. Emphasis has been given to describe and discuss the experimental conditions of the Pd-catalyzed (S.-M.) cross-coupling reactions also outlining the methods used to prepare the reactants. A focus has also been set on the biological and pharmacological properties of the reported natural products as well as on the most significant steps of the reported total syntheses

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Enantioselective total syntheses of cedrelin A and methylated paralycolin B using Pd-catalyzed asymmetric intramolecular Friedel–Crafts allylic alkylation of phenols

Cited by 13 publications

References 21 publications

Applications of Transition‐Metal‐Catalyzed Asymmetric Allylic Substitution in Total Synthesis of Natural Products: An Update

Applications of Transition‐Metal‐Catalyzed Asymmetric Allylic Substitution in Total Synthesis of Natural Products: An Update

Applications of Friedel–Crafts reactions in total synthesis of natural products

Recent Applications of Phosphane-based Palladium Catalysts in Suzuki-Miyaura Reactions Involved in Total Syntheses of Natural Products

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