Total synthesis of nagilactone F, a biologically active norditerpenoid dilactone isolated from Podocarpus nagi

Hayashi, Yûji; Matsumoto, Takeshi; Nishizawa, Masatoyo; Togami, Masatoshi; HYONO, T.; Nishikawa, Naomi; Uemura, Motokazu; Sakan, Takeo

doi:10.1021/jo00139a008

Cited by 31 publications

(22 citation statements)

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“…[57] Eine Heteroatom-Variante der [6p]-Photocyclisierung, näm-lich die Reaktion einer a,b,g,d-ungesättigten Carbonsäure zum b,g-ungesättigten Lacton, wurde in einer Synthese von Nagilacton F eingesetzt. [58] Die Umkehrung der [6p]-Photocyclisierung, also die konrotatorische Öffnung von 1,3-Cyclohexadienen, führt zur Spaltung eines Sechsrings. [59,60] [65] und Nauclefin (Parvin) [66] hergestellt.…”

Section: Aufsätzeunclassified

Photochemische Reaktionen als Schlüsselschritte in der Naturstoffsynthese

2011

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Photochemische Reaktionen bereichern in signifikanter Weise das Repertoire zur Knüpfung von Kohlenstoff‐Kohlenstoff‐Bindungen und machen ungewöhnliche, auf herkömmlichem Weg nicht erhältliche Molekülgerüste zugänglich. In diesem Aufsatz werden die wichtigsten Umsetzungen der Photochemie vorgestellt, die auf breiter Front Einzug in die Naturstoffsynthese gehalten haben. Beispielhaft werden einzelne Totalsynthesen diskutiert, wobei besonderes Augenmerk auf den photochemischen Schlüsselschritt sowie dessen Stereoselektivität gerichtet ist. Dabei wird das photochemisch erzeugte Molekül in Relation zur Struktur des Naturstoffs gebracht, und Folgereaktionen werden, wo notwendig, illustriert und klassifiziert.

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Section: Aufsätzeunclassified

Photochemische Reaktionen als Schlüsselschritte in der Naturstoffsynthese

2011

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“…More recently, Kelly and co‐workers applied the [6π] photocyclization of an ortho ‐pyridinylstyrene to the synthesis of the alkaloid santiagonamine 57. A heteroatom variant of the [6π] photocyclization, namely the reaction of an α,β,γ,δ‐unsaturated carboxylic acid to an β,γ‐unsaturated lactone, was utilized in a synthesis of nagilactone F 58…”

Section: Photocyclizationsmentioning

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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“…zur Synthese des Alkaloids Santiagonamin angewendet 57. Eine Heteroatom‐Variante der [6π]‐Photocyclisierung, nämlich die Reaktion einer α,β,γ,δ‐ungesättigten Carbonsäure zum β,γ‐ungesättigten Lacton, wurde in einer Synthese von Nagilacton F eingesetzt 58…”

Section: Photocyclisierungenunclassified

Book review

Larsson¹

2001

Int J of Quantum Chemistry

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Volume 1 has the subtitle Basic Problems and ModelSystems and consists of five parts. The first two parts deal with density matrices and electron correlation. Kozmutza, Kapui, and Udvardi have carried out an interesting study of transferability of electron correlation effects in a localized representation. Examples are taken from CH and CC bonds in polyenes and noble-gas clusters. Most of the other chapters consist of improved calculations of correlation effects on various properties. The last chapter, by Kaplan et al., is different since it describes calculations on a cluster of a superconducting CuO system. Here the chances to obtain a converged and meaningful end result are not great, but the authors make a brave and far-reaching attempt using second-order Møller-Plesset (MP2) method with careful inclusion of the Madelung corrections. Three copper atoms are included, but the two outermost ones are missing one of their oxygen neighbors. The hole states, due to the missing electron in the Cu 3d subshell, is localized on different atoms and in different orbitals, depending on calculation method. This confusing picture seems to be unavoidable and has been seen before in studies by Broer and Nieuwpoort and other works cited in the Kaplan paper.Part III, containing "Relativistic Formulations," is impressive in both width and depth. Particularly the first two chapters, written by Kaldor and Eliav and by Karwowski et al., are interesting reading and give a good summary of the field.

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Total synthesis of nagilactone F, a biologically active norditerpenoid dilactone isolated from Podocarpus nagi

Cited by 31 publications

References 0 publications

Photochemische Reaktionen als Schlüsselschritte in der Naturstoffsynthese

Photochemische Reaktionen als Schlüsselschritte in der Naturstoffsynthese

Corrosion News

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