Natural Product Synthesis by C−H Activation

Sinha, Sucharita; Zanoni, Giuseppe; Maiti, Debabrata

doi:10.1002/ajoc.201800203

Cited by 109 publications

(31 citation statements)

References 147 publications

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“… 9 Using their approach as inspiration, we were able to develop a shorter route to 12 leveraging the tools of C–H functionalization. 10 Thus, we could prepare pyrrole dibromide 18 via iron-catalyzed C–H methoxycarbonylation 11 of commercial ester 17 , followed by dibromination ( Scheme 1 ). 12 For the other partner, we could advance 5-chloroindole ( 19 ) to C-3 boronic ester 20 through an efficient Ir-catalyzed C–H borylation sequence.…”

Section: Resultsmentioning

confidence: 99%

Total synthesis of (+)-spiroindimicin A and congeners unveils their antiparasitic activity

et al. 2021

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Section: Resultsmentioning

confidence: 99%

Total synthesis of (+)-spiroindimicin A and congeners unveils their antiparasitic activity

et al. 2021

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“…Apart from the available methods, over the years, the methods available for the introduction of functionality over the aromatic system through C-H activation has been extensively and robustly explored and employed in the synthesis of natural products and like analogues. [97] Strategies from the early heteroatom-directed radical chemistry, carbene insertion to recent transition metal catalyzed C-H activation approaches. The in- creasing importance and relevance of "economy" in the design and execution of synthesis has arguably propelled the area of C-H functionalization beyond curiosity.…”

Section: Discussionmentioning

confidence: 99%

Mycophenolic Acid: Biogenesis, Compound Isolation, Biological Activity, and Historical Advances in Total Synthesis

et al. 2019

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The 6‐alkyl‐2,4‐dihydroxybenzoate moiety known commonly as resorcylate occurs widely as a building block in various fused cyclic systems of bioactive natural products and analogues. Among these many isolated active molecules, mycophenolic acid (MPA) was one of the most studied for its structural features and its potential biological activity. This perspective article portrays the unique biosynthetic interrelationships of polyketide formations in to resorcylates, which are implemented by recent biomimetic/chemical synthetic investigations of the natural product target. The resorcylate, MPA have remained as interesting targets for total synthesis in many laboratories worldwide. There are 13 syntheses reported for MPA to date (Scifinder search). The synthetic strategies for this potential lead compound was an evolution of various methods from generating the highly‐substituted aromatic system via employing simple and commercially available materials to the catalytic methods employed which always involve linear sequences; convergent approaches to the most important protecting group‐free syntheses are also briefly documented in this critical review. This natural product has been the subject of considerable synthetic study. Most reported total syntheses employ 6‐alkyl‐2,4‐hydroxybenzoic acids (lactones) as intermediates and proceed via stepwise derivatization to introduce other functionalities.

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“…In particular, the exploitation of Earth-abundant transition metals as catalysts for new approaches to C-H functionalization offers sustainable solutions to many challenges in contemporary synthesis. 1 The development of C-H functionalization methods supplements conventional organic transformations by al-lowing access to previously unexploited retrosynthetic disconnections. As a result of recent developments, the introduction of functional complexity into a molecule by functionalization of C-H bonds is an increasingly viable strategy for creating diverse molecular structures.…”

Section: Introductionmentioning

confidence: 99%

Redox-Neutral Propargylic C–H Functionalization by Using Iron Catalysis

Durham¹,

Wang²,

Wang³

2020

Synlett

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In spite of their rich stoichiometric chemistry, cyclopentadienyliron(II) dicarbonyl complexes are rarely used as catalysts in organic synthesis. Inspired by precedents in the chemistry of cationic olefin complexes and neutral allylmetal species, our group has developed a coupling of alkynes or alkenes with aldehydes and other carbonyl electrophiles to give homopropargylic and homoallylic alcohols, respectively, by using a substituted cyclopentadienyliron(II) dicarbonyl complex as the catalyst. In this article, we first contextualize this development within the conceptual background of C–H functionalization chemistry and relative to key stoichiometric precedents. We then give an account of our group’s discovery and development of the catalytic α-functionalization of alkenes and alkynes with electrophilic reagents.Introduction Preliminary Stoichiometric WorkHydroxyalkylation Development and ScopeConclusions and Future Directions

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Natural Product Synthesis by C−H Activation

Cited by 109 publications

References 147 publications

Total synthesis of (+)-spiroindimicin A and congeners unveils their antiparasitic activity

Total synthesis of (+)-spiroindimicin A and congeners unveils their antiparasitic activity

Mycophenolic Acid: Biogenesis, Compound Isolation, Biological Activity, and Historical Advances in Total Synthesis

Redox-Neutral Propargylic C–H Functionalization by Using Iron Catalysis

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