Synthesis of (+)-Pancratistatins via Catalytic Desymmetrization of Benzene

Hernandez, Lucas W.; Pospech, Jola; Klöckner, Ulrich; Bingham, Tanner W.; Šarlah, David

doi:10.1021/jacs.7b10351

Cited by 84 publications

(53 citation statements)

References 57 publications

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“…Shuai Zou, et al developed method for photo catalytic synthesis of 3-position substituted 3,4-dihydroisoquinolin- offer the advantage over other methods is that it does not require the protection deprotecton. [101]…”

Section: Scheme 42 Synthesis 4-hydroxyalkyl-substituted 34-dihydroimentioning

confidence: 99%

Recent Advances in Synthesis of 3,4‐Dihydroisoquinolin‐1(2H)‐one

Kulkarni

Gaikwad

2020

ChemistrySelect

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The 3,4‐dihydroisoquinolin‐1(2H)‐one motifs found in many natural products, synthetic molecules with a diverse range of the biological activities and represent a privilege scaffold. Thereby the number of the innovative synthetic methodologies has been reported for constructions of this scaffold, which includes metal catalyzed and metal free method, multicomponent, domino one pot protocol, oxidation, Friedel‐Crafts type of cyclization. In the recent years many general protocols for the construction of this scaffold were reported in the literature and there is no focussed individual review for the 3,4‐dihydroisoquinolin‐1(2H)‐one since 2001. This review focuses on the reports describing the new method for the synthesis of 3,4‐dihydroisoquinolin‐1(2H)‐one, published since 2001 to till date. In this review, we approach method of the synthesis of 3,4‐dihydroisoquinolin‐1(2H)‐one according to the strategy used for its synthesis, which includes, the intramolecular cyclization of carbamate/ urea/ thiourea/ isocyanate/ azidoamide, carbonylation/ carbomylation/ carbonyl insertion, metal catalyzed protocols by C−H activation by directing group, metal free domino procedures and oxidations of isoquinoline derivatives that were included in recent publications. Moreover, the reports published since 2001 for the synthesis of the chiral 3,4‐dihydroisoquinolin‐1(2H)‐one are included.

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Section: Scheme 42 Synthesis 4-hydroxyalkyl-substituted 34-dihydroimentioning

confidence: 99%

Recent Advances in Synthesis of 3,4‐Dihydroisoquinolin‐1(2H)‐one

Kulkarni

Gaikwad

2020

ChemistrySelect

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“…[56] Yet, despite the many approaches towardst he Amaryllidaceae isocarbostyril alkaloids, there has not been ag eneral strategy to access the entire class in as cal-able, concise, and versatile manner.W et ook on this challenge and it was made possible by the development of an asymmetric dearomative carboamination reactiono fb enzene to set the first two stereocenters, allowing for stereoselective installation of the remaining four (Scheme 16). [57] Our synthesis began with the key dearomativec arboamination of benzene (204)w ith MTAD (205)a nd benzodioxole-derived Grignardr eagent 206 in 65 %y ield and 98:2 e.r., delivering the desired diene 207 on 11.4 gs cale. It was important to perform the methylative quencho ft his reactiona st he acidic hydrazyl proton exhibited undesiredd irecting-group effects Scheme15.…”

Section: Pancratistatin (Sarlah 2017)mentioning

confidence: 99%

Empowering Synthesis of Complex Natural Products

Hernandez

Šarlah

2019

Chemistry A European J

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Synthesis of natural products remains a daring task. Their richly diverse and intricate structures often encompass a large degree of unsaturation, contain fused and/or bridged rings, or possess numerous stereogenic centers. Thus, their preparation requires significant synthetic overhead, detracting from their overall practicality as well as hampering the ability of medicinal chemists to synthesize derivatives for pharmaceutical optimization and structure‐activity relationship studies. The purpose of this Minireview is to showcase recent examples of efficient total syntheses. Emphasis was not given to the evaluation of ideality or economies (quality), but rather to the practicality (quality with quantity).

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“…The observed regiochemical outcomes are likely a result of the difference in preferred structure of the cationic metal intermediates. Specifically, the Ni‐complex forms the η 5 ‐cyclohexadienyl‐like intermediate II , with greater positive charge localized on the termini of the η 5 ‐system, while the Pd‐complex adopts the η 3 ‐allyl‐like structure III , with the incoming nucleophile reacting at the remote site from the urazole . The observed stereoselectivity was in accordance with the general trends of transition metal catalyzed allylic substitution .…”

Section: Figurementioning

confidence: 99%

Palladium‐Catalyzed Dearomativesyn‐1,4‐Carboamination with Grignard Reagents

et al. 2019

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A protocol for palladium‐catalyzed dearomative functionalization of simple, nonactivated arenes with Grignard reagents has been established. This one‐pot method features a visible‐light‐mediated [4+2] cycloaddition between an arene and an arenophile, and subsequent palladium‐catalyzed allylic substitution of the resulting cycloadduct with a Grignard reagent. A variety of arenes and Grignard reagents can participate in this process, forming carboaminated products with exclusive syn‐1,4‐selectivity. Moreover, the dearomatized products are amenable to further elaborations, providing functionalized alicyclic motifs and pharmacophores. For example, naphthalene was converted into sertraline, one of the most prescribed antidepressants, in only four operations. Finally, this process could also be conducted in an enantioselective fashion, as demonstrated with the desymmetrization of naphthalene.

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Synthesis of (+)-Pancratistatins via Catalytic Desymmetrization of Benzene

Cited by 84 publications

References 57 publications

Recent Advances in Synthesis of 3,4‐Dihydroisoquinolin‐1(2H)‐one

Recent Advances in Synthesis of 3,4‐Dihydroisoquinolin‐1(2H)‐one

Empowering Synthesis of Complex Natural Products

Palladium‐Catalyzed Dearomativesyn‐1,4‐Carboamination with Grignard Reagents

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