Total Synthesis of Ustiloxin D Utilizing an Ammonia–Ugi Reaction

Brown, Aaron; Churches, Quentin I.; Hutton, Craig A.

doi:10.1021/acs.joc.5b01519

Cited by 28 publications

(19 citation statements)

References 31 publications

(14 reference statements)

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“…Racemic and commercial 2‐methylbutanal led to the Ile Ugi product 5 h and the Ile analogue 6 h as a mixture of two diastereomers in 1:1 ratio (Table , 5 h and 6 h ). This lack of stereoselectivity is a well‐established feature of Ugi reactions …”

Section: Resultsmentioning

confidence: 99%

α‐Amino Acid‐Isosteric α‐Amino Tetrazoles

Zhao

Kurpiewska

Kalinowska‐Tłuścik

et al. 2016

Chemistry A European J

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The synthesis of all 20 common natural proteinogenic and 4 otherα-amino acid-isosteric α-amino tetrazoles has been accomplished, whereby the carboxyl group is replaced by the isosteric 5-tetrazolyl group. The short process involves the use of the key Ugi tetrazole reaction followed by deprotection chemistries. The tetrazole group is bioisosteric to the carboxylic acid and is widely used in medicinal chemistry and drug design. Surprisingly, several of the common α-amino acid-isosteric α-amino tetrazoles are unknown up to now. Therefore a rapid synthetic access to this compound class and non-natural derivatives is of high interest to advance the field.

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Section: Resultsmentioning

confidence: 99%

α‐Amino Acid‐Isosteric α‐Amino Tetrazoles

Zhao

Kurpiewska

Kalinowska‐Tłuścik

et al. 2016

Chemistry A European J

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“…After a decade, Hutton et al. achieved the total synthesis of ustiloxin D ( 109 ) in a convergent manner by the preparation of the t ‐alkyl aryl ether through a highly stereoselective AAS of the dopa and isoleucine residues [103] . They started the reaction with the preparation of β‐OH dopa derivative 116 .…”

Section: Palladium‐catalyzed Aas Reactionsmentioning

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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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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“…Hutton'sa pproach:H utton and co-workers in 2015 reported the synthesis of Ustiloxin D( 15). [46] Asymmetric allylic alkylation, ammonia-Ugi reaction, followed by cyclization and global deprotection are the key steps involved in the synthesis of Ustiloxin D( 15)f rom b-hydroxydopa derivative 178 (Scheme 15). Compound 178 was first synthesized from 176 and 177 by using Joullie's method.…”

Section: Isolation Characterizationa Nd Biological Activitymentioning

confidence: 99%

A Comparative Synthetic Strategy Perspective on α‐Amino Acid‐ and Non‐Amino Acid‐Derived Synthons towards Total Syntheses of Selected Natural Macrolides

Manda

Tripathi

Ghoshal

et al. 2020

Chemistry A European J

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other methods derived from miscellaneous synthons towards the total synthesiso fn on-peptidic macrolides.T he synthetic routes and the key strategies involved in the total syntheses of ten natural macrolides have been discussed. Both the amino acid-derived and non-amino acid-derived synthetic routes have been illustratedt op resentacomparative study between the two approaches.Scheme3.Prusov's approach towards the total synthesis of Ripostatin B( 5).Scheme4.To tal synthesis of Ripostatin B( 5)b yA ltmann's approach. Figure 3. Biologically active analogues of Ripostatin.

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Total Synthesis of Ustiloxin D Utilizing an Ammonia–Ugi Reaction

Cited by 28 publications

References 31 publications

α‐Amino Acid‐Isosteric α‐Amino Tetrazoles

α‐Amino Acid‐Isosteric α‐Amino Tetrazoles

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

A Comparative Synthetic Strategy Perspective on α‐Amino Acid‐ and Non‐Amino Acid‐Derived Synthons towards Total Syntheses of Selected Natural Macrolides

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