Improved Procedure for the Enantiometric Synthesis of 1-Hydroxy/acetoxy-2,6-diaryl-3,7-dioxabicyclo[3.3.0] octane Lignans: Total Syntheses of (+)-Paulownin, (+)-Phrymarin I and (+)-Phrymarin II

Ishibashi, Fumito; Hayashita, Mami; Okazaki, Momotoshi; Shuto, Yoshihiro

doi:10.1271/bbb.65.29

Cited by 13 publications

(8 citation statements)

References 11 publications

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“…Examples of this type have been applied in the synthesis of (±)-paulownin ( 493 , Scheme 88 ) 372 and the structurally related (+)-phrymarin I and (+)-phrymarin II. 373 …”

Section: Norrish-type Photoreactionsmentioning

confidence: 99%

Photochemical Approaches to Complex Chemotypes: Applications in Natural Product Synthesis

2016

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The use of photochemical transformations is a powerful strategy that allows for the formation of a high degree of molecular complexity from relatively simple building blocks in a single step. A central feature of all light-promoted transformations is the involvement of electronically excited states, generated upon absorption of photons. This produces transient reactive intermediates and significantly alters the reactivity of a chemical compound. The input of energy provided by light thus offers a means to produce strained and unique target compounds that cannot be assembled using thermal protocols. This review aims at highlighting photochemical transformations as a tool for rapidly accessing structurally and stereochemically diverse scaffolds. Synthetic designs based on photochemical transformations have the potential to afford complex polycyclic carbon skeletons with impressive efficiency, which are of high value in total synthesis.

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“…Examples of this type have been applied in the synthesis of (±)-paulownin ( 493 , Scheme 88 ) 372 and the structurally related (+)-phrymarin I and (+)-phrymarin II. 373 …”

Section: Norrish-type Photoreactionsmentioning

confidence: 99%

Photochemical Approaches to Complex Chemotypes: Applications in Natural Product Synthesis

2016

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“…[127] Weitere Naturstoffe, deren Fünfringe durch Norrish-Yang-Cyclisierung aufgebaut wurden, sind in Abbildung 3 gezeigt. Dazu gehören (AE )-Cuparen (81), [128] das racemische Pheromon 82 [129] sowie (AE )-Isoretronecanol (83).…”

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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“…In 2001, Ishibashi published a synthesis of (+)-paulownin, (+)-phrymarin I, and (+)-phrymarin II (Ishibashi et al, 2001). The report featured an elegant photochemical reaction that was developed by Kraus in 1990 (Kraus andChen, 1990).…”

Section: Synthetic Studies Toward Haedoxan-like Moleculesmentioning

confidence: 99%

A Synthetic View on Haedoxans and Related Neolignans From Phryma leptostachya

et al. 2020

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Haedoxans are a series of sesquilignan natural products isolated from the traditional insecticidal plant Phryma leptostachya. Given their significant insecticidal activity, haedoxans and related analogs have been considered as potential agents for plant defense. Moreover, these compounds also exhibit promising antifungal, antibacterial, and anticancer activities. The present paper is a review of the structure, biological activity, and chemical synthesis of naturally occurring haedoxan-like molecules.

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Improved Procedure for the Enantiometric Synthesis of 1-Hydroxy/acetoxy-2,6-diaryl-3,7-dioxabicyclo[3.3.0] octane Lignans: Total Syntheses of (+)-Paulownin, (+)-Phrymarin I and (+)-Phrymarin II

Cited by 13 publications

References 11 publications

Photochemical Approaches to Complex Chemotypes: Applications in Natural Product Synthesis

Photochemical Approaches to Complex Chemotypes: Applications in Natural Product Synthesis

Photochemische Reaktionen als Schlüsselschritte in der Naturstoffsynthese

A Synthetic View on Haedoxans and Related Neolignans From Phryma leptostachya

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