Enantioselective Total Synthesis of (+)-Dihydro-β-erythroidine

Clementson, Sebastian; Jessing, Mikkel; Pedersen, Henrik; Vital, Paulo; Kristensen, Jesper L.

doi:10.1021/jacs.9b04626

Cited by 19 publications

(14 citation statements)

References 44 publications

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“…The allylation of nucleophilic carbon centers is one of the most useful methods for the formation of C(sp 3 )-C(sp 3 ) linkages [3][4][5][6][7][8] . As a result, it has been widely applied in the synthesis of bioactive compounds and natural products [9][10][11][12][13][14][15] . For decades, tremendous effort has been devoted to developing new and efficient methods for allylic alkylation.…”

mentioning

confidence: 99%

Transition-metal-free allylation of 2-azaallyls with allyl ethers through polar and radical mechanisms

et al. 2021

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Allylation of nucleophiles with highly reactive electrophiles like allyl halides can be conducted without metal catalysts. Less reactive electrophiles, such as allyl esters and carbonates, usually require a transition metal catalyst to facilitate the allylation. Herein, we report a unique transition-metal-free allylation strategy with allyl ether electrophiles. Reaction of a host of allyl ethers with 2-azaallyl anions delivers valuable homoallylic amine derivatives (up to 92%), which are significant in the pharmaceutical industry. Interestingly, no deprotonative isomerization or cyclization of the products were observed. The potential synthetic utility and ease of operation is demonstrated by a gram scale telescoped preparation of a homoallylic amine. In addition, mechanistic studies provide insight into these C(sp3)–C(sp3) bond-forming reactions.

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confidence: 99%

Transition-metal-free allylation of 2-azaallyls with allyl ethers through polar and radical mechanisms

et al. 2021

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“…Kristensen, Vital and co‐workers reported the an elegant first total synthesis of (+)‐dihydro‐ β ‐erythroidine 381 (Scheme 50), a powerful nicotine acetylcholine receptor (nAChR) antagonists, produce by the seeds of the Erythrina americana family of Mexican coral plants [231] . In this synthetic approach, RCM was employed in the construction of bicyclic alkaloid core structure.…”

Section: Ring‐closing Metathesis (Rcm)mentioning

confidence: 99%

Metathesis Reactions in Natural Product Fragments and Total Syntheses

et al. 2022

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The passion of total‐ and fragments syntheses of natural products always remained one of the top priorities among the synthetic chemists worldwide. Due their curiosity toward the complexity of molecules of living nature and their endeavour to imitate them in laboratory; limitless arrays of natural products have been extracted, architecturally‐elucidated, synthesized, and chronicled by utilizing various synthetic methodologies in different fashions. Frequently, the synthesis of complex natural products proceed with inscrutable synthetic challenges, which can be circumvented either by modification of previously developed synthetic methods or by formulating a new one. In this way, a myriad of powerful synthetic reactions have been developed since the genesis of the logic of chemical synthesis. Amongst them, metathesis tactics discovered unexpectedly in the 1950s (Nobel Prize in 2005), have incredibly influenced and changed the landscape of the art of the total and formal synthesis in the last three A. H. Hoveyda, A. R. Zhugralin, me abruptly as compared to other developed transformations or their modified forms. In this particular review article, we envisioned to report a comprehensive detail of the metathetic tools involved in both total and fragments synthesis of natural products in the years 2018 and 2019 along with an overview of 2017.

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“…More than 140 erythrina alkaloids have been isolated and identified to date, which exhibit broad bioactivities, including hypotensive, sedative, central nervous system (CNS) depressant, anti-HIV and curare-like activity. 10,[39][40][41] Hence, diverse synthetic strategies toward erythrina alkaloids have been developed by synthetic communities [39][40][41][42][43][44][45][46][47][48][49][50][51][52] from the early pioneers Belleau, Modndon, and Prelog in the 1950s, to Tsuda in the 1980s; recent contributions from Padwa, Tietze, Reisman, Kim, You, Tu, Zhang, and others further advance the research area [39][40][41] and inspire continued synthetic interest, as amplified by the latest studies from the groups of Fukayama and Kitamura, 47 Booker-Miburn, 48 Vital and Kristensen, 49 Tong and Wang, 50 Xu, 51 and She 52 . In contrast to the previously reported synthetic strategies, we speculated that the target molecules could be synthesized through a novel aza-quaternary-carbon-center-guided disconnected strategy.…”

Section: Collective Total Syntheses Of Erythrina Alkaloidsmentioning

confidence: 99%

Exploration of Oxidative Ritter-Type Reaction of α-Arylketones and Its Application for the Collective Total Syntheses of Erythrina Alkaloids

Chen

Tang

et al. 2022

CCS Chem

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Although the classical Ritter reaction has been widely applied to prepare sterically hindered amides since 1948, it has intrinsic problems, such as harsh reaction conditions, the multistep preparation of synthetic precursors, and the use of solvent quantities of nitrile. In particular, only a few examples of the total syntheses of natural products using the Ritter reaction as a key step have been reported to date. In this article, an oxidative Ritter-type reaction of α-arylketones was developed to efficiently construct a sterically hindered N-acyl aza-quaternary carbon moiety. The current transformation features the use of 10 equivalents of nitriles, a broad substrate scope (81 examples), a short reaction time, and mild reaction conditions; notably, both of the use of a limited amount of nitriles and the producing carbocation intermediates via the C-H bond oxidation strategy address two intractable problems of the classical Ritter reaction. Furthermore, based on an unprecedented synthetic strategy using this oxidative Ritter reaction to construct a C-5 aza-quaternary carbon center, the collective total syntheses of erythrina alkaloids, including erysotramidine, 11-α-methoxyerysotramidine, 11-β-hydroxyerysotramidine, erytharbine, the proposed 11-βmethoxyerysotramidine and 10,11-dioxoerysotramidine, and the unnatural 11-α-hydroxyerysotramidine, have been completed using a common precursor through a one-step chemical transformation.

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Enantioselective Total Synthesis of (+)-Dihydro-β-erythroidine

Cited by 19 publications

References 44 publications

Transition-metal-free allylation of 2-azaallyls with allyl ethers through polar and radical mechanisms

Transition-metal-free allylation of 2-azaallyls with allyl ethers through polar and radical mechanisms

Metathesis Reactions in Natural Product Fragments and Total Syntheses

Exploration of Oxidative Ritter-Type Reaction of α-Arylketones and Its Application for the Collective Total Syntheses of Erythrina Alkaloids

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