A Concise Total Synthesis of (<i>R</i>)‐Puraquinonic Acid

Tiong, E. A.; Rivalti, Daniel; Williams, Benjamin M.; Gleason, James L.

doi:10.1002/anie.201208792

Cited by 39 publications

(23 citation statements)

References 30 publications

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“…57 Existing methods for the creation of quaternary stereocentres in acyclic systems through the formation of stereodefined enolate structures covered so far clearly demonstrate the extraordinary levels of sophistication reached in synthetic organic chemistry with respect to the creation of one carboncarbon bond per chemical step.…”

Section: Scheme 19mentioning

confidence: 99%

Stereodefined acyclic trisubstituted metal enolates towards the asymmetric formation of quaternary carbon stereocentres

Minko

Marek

2014

Chem. Commun.

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Reactions that involve metal enolate species are amongst the most versatile carbon-carbon bond forming processes available to synthetic chemists. Enolate species are involved in a multitude of powerful applications in asymmetric organic synthesis, but the generation of fully substituted enolates in a geometrically defined form is not easily achieved especially in acyclic systems. In this Feature Article we focus on the most prominent examples reported in the literature describing the formation of highly diastereo- and enantiomerically enriched quaternary stereocentres in acyclic molecules derived from stereodefined non-cyclic trisubstituted metal enolates.

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Section: Scheme 19mentioning

confidence: 99%

Stereodefined acyclic trisubstituted metal enolates towards the asymmetric formation of quaternary carbon stereocentres

Minko

Marek

2014

Chem. Commun.

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“…The RCEYM/DA/aromatization sequence was applied to the synthesis of puraquinonic acid, a fungal metabolite possessing mild anticancer activity. 38 In spite of its apparently simple molecular structure, the enantioselective synthesis of this natural compound has proven to be a demanding challenge. By exploiting a bicyclic thioglycolate lactam as a chiral auxiliary for the construction of the quaternary stereocenter of enyne 36, Gleason et al 38 succeeded in the preparation of pure (R)-puraquinonic acid in 12 steps and a remarkable 20% overall yield (Scheme 11).…”

Section: Review Synthesismentioning

confidence: 99%

Recent Advances in One-Pot Enyne Metathesis Processes for the Preparation of Biologically and Medicinally Relevant Compounds

Bernardi

Colombo²,

Serra³

2020

Synthesis

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Enyne metathesis reactions are powerful tools for the preparation of a wide range of synthetic and natural chemical substances with increasing efficiency and environmental sustainability. The driving force of the reaction is the formation of a stable conjugated system, i.e., a diene, which through further functionalization steps can be used for the construction of skeletally complex molecular architectures. These concepts are exploited to design cascade reaction sequences, where multiple rings can be formed in a one-pot fashion by combining metathetic protocols with various chemical transformations. The strong correlation between synthetic organic chemistry and medicinal chemistry prompted us to review the most notable approaches for the synthesis of biologically relevant compounds via enyne metathesis-based one-pot processes. With the aim to provide a modern and practical overview, by taking into consideration the scientific literature on this topic, we have focused the majority of our attention on the research performed in the last decade. This review covers the literature from 2003 to 2020.1 Introduction2 Ethylene-Mediated Processes3 RCEYM/CM and CEYM/RCM Processes4 Enyne Metathesis/Diels–Alder-Based Processes5 RCM of Dienynes6 RCM of Tethered Dienynes7 Relay Metathesis8 Ring-Rearrangement Metathesis9 RCEYM/Transition-Metal-Catalyzed C–C Bond-Forming Processes10 Conclusions11 List of Acronyms

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“…A method to form quaternary stereocenters, based on the stereoselective generation and alkylation of α,α-disubstituted amide enolates derived from bicyclic thioglycolate lactam 209, was used in a total synthesis of (R)-puraquinonic acid (13AGE3442). In a simultaneous nucleophilic substitution and heterocyclization process, 2-[(5-bromo-2-chloro-6-aminopyrimidin-4-yl)methylthio]anilines and a variety of secondary amines (R 1 2 NH) reacted to form 5,7-diamino-5,11-dihydropyrimido[5,4-e] [1,4]benzothiazepines 210 (13HCO401).…”

Section: Thiazepines and Derivativesmentioning

confidence: 99%

Seven-Membered Rings

Ryan

Smith

Hyland

et al. 2014

Progress in Heterocyclic Chemistry

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A Concise Total Synthesis of (R)‐Puraquinonic Acid

Abstract: Scheme 1. Structure of (R)-puraquinonic acid and the illudalane skeleton.Scheme 2. A bicyclic lactam auxiliary for selective quaternary stereocenter formation. LDA = lithium diisopropylamide.Scheme 3. Retrosynthetic approach to (R)-puraquinonic acid.

Cited by 39 publications

References 30 publications

Stereodefined acyclic trisubstituted metal enolates towards the asymmetric formation of quaternary carbon stereocentres

Stereodefined acyclic trisubstituted metal enolates towards the asymmetric formation of quaternary carbon stereocentres

Recent Advances in One-Pot Enyne Metathesis Processes for the Preparation of Biologically and Medicinally Relevant Compounds

Seven-Membered Rings

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