Total synthesis of (+)-ligudentatol via Photoaddition-Fragmentation-Aromatic Annulation sequence

Haddad, Nizar; Salman, Husein

doi:10.1016/s0040-4039(97)21374-2

Cited by 11 publications

(5 citation statements)

References 17 publications

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“…The intramolecular [2 + 2] photocycloaddition of 2,3-dihydro-4 H -pyran-4-ones was applied by Haddad and Salman to the synthesis of (+)-ligudentatol. − More recently, Porco Jr. and co-workers employed the intramolecular [2 + 2] photocycloaddition of the pyran-2,4-dione rac - 266 to elucidate its constitution and relative configuration via a crystal structure of product rac - 267 (Scheme ). …”

Section: Direct Excitation and Sensitizationmentioning

confidence: 99%

Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions

et al. 2016

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The [2 + 2] photocycloaddition is undisputedly the most important and most frequently used photochemical reaction. In this review, it is attempted to cover all recent aspects of [2 + 2] photocycloaddition chemistry with an emphasis on synthetically relevant, regio-, and stereoselective reactions. The review aims to comprehensively discuss relevant work, which was done in the field in the last 20 years (i.e., from 1995 to 2015). Organization of the data follows a subdivision according to mechanism and substrate classes. Cu(I) and PET (photoinduced electron transfer) catalysis are treated separately in sections 2 and 4, whereas the vast majority of photocycloaddition reactions which occur by direct excitation or sensitization are divided within section 3 into individual subsections according to the photochemically excited olefin.

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Section: Direct Excitation and Sensitizationmentioning

confidence: 99%

Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions

et al. 2016

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“…An enantioselective synthesis of natural (+)‐ligudentatol ( 1 ) was previously reported by Haddad and Salman, who devised a [2+2] photochemical access to the phenolic motif 5. Our synthetic route to ligudentatol features the construction of a phenolic core by facile aromatization of highly functionalized decalin system iii that is accessible by seleno transfer radical cyclization of iv (Scheme ) 6.…”

Section: Methodsmentioning

confidence: 94%

Enantiospecific Synthesis and Cytotoxicity Evaluation of Ligudentatol: A Programmed Aromatization Approach to the 2,3,4‐Trisubstituted Phenolic Motif via Visible‐Light‐Mediated Group Transfer Radical Cyclization

Moustafa

Suizu

Aoyama

et al. 2014

Chemistry An Asian Journal

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A facile enantiospecific approach to (+)-ligudentatol (1) and (-)-ligudentatol (ent-1) is reported. The approach features the construction of a trisubstituted phenolic motif fused to a chiral aliphatic ring by a sequence of visible-light-mediated radical seleno transfer cyclization, bromination, concomitant selenoxide elimination-dehydrobromination, and demethoxycarbonylation, namely, a programmed aromatization. Biological evaluation of the enantiomers of ligudentatol obtained by the present route revealed for the first time their cytotoxicity towards various cancer cell lines.

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“…The Lewis acid catalyzed retro‐aldol fragmentation of dihydropyrane photoadducts yields oxygenated products that can be condensed to give benzoid arenes. An application of this inventive sequence can be found in the synthesis of (+)‐ligudentatol ( 334 ) 422…”

Section: [2+2] Photocycloadditions Of Olefinsmentioning

confidence: 99%

Corrosion News

2007

Materials & Corrosion

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Photochemical reactions contribute in a significant way to the existing repertoire of carbon–carbon bond‐forming reactions by allowing access to exceptional molecular structures that cannot be obtained by conventional means. In this Review, the most important photochemical transformations that have been employed in natural product synthesis are presented. Selected total syntheses are discussed as examples, with particular attention given to the photochemical key step and its stereoselectivity. The structural relationship between the photochemically generated molecule and the natural product is shown, and, where necessary, the consecutive reactions in the synthesis are illustrated and classified.

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Total synthesis of (+)-ligudentatol via Photoaddition-Fragmentation-Aromatic Annulation sequence

Cited by 11 publications

References 17 publications

Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions

Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions

Enantiospecific Synthesis and Cytotoxicity Evaluation of Ligudentatol: A Programmed Aromatization Approach to the 2,3,4‐Trisubstituted Phenolic Motif via Visible‐Light‐Mediated Group Transfer Radical Cyclization

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Total synthesis of (+)-ligudentatol via Photoaddition-Fragmentation-Aromatic Annulation sequence

Cited by 11 publications

References 17 publications

Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions

Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions

Enantiospecific Synthesis and Cytotoxicity Evaluation of Ligudentatol: A Programmed Aromatization Approach to the 2,3,4‐Trisubstituted Phenolic Motif via Visible‐Light‐Mediated Group Transfer Radical Cyclization

Corrosion News

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Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions

Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions