The total synthesis of .alpha.- and .beta.-Bourbonene

White, James D.; Gupta, D. N.

doi:10.1021/ja01024a040

Cited by 53 publications

(14 citation statements)

References 9 publications

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“…We thus recorded antennal responses of B. psenes to synthetic versions (purchased at Sigma-Aldrich ® , Bellefonte, PA, USA) of b-caryophyllene [(-)-trans-caryophyllene; purity: 99%)], linalool [(±)-linalool; purity: 97%], linalool oxide (mixture of isomers; purity > 97%), germacrene D (purity: 40%), a-copaene [(-)-a-copaene; purity: 95%)]. b-bourbonene was not tested as it is not commercially available and not easily synthesised (White & Gupta 1968;Tomioka et al 1982). Each wasp was tested for all compounds in a random order.…”

Section: Sensory Tests Using Electrophysiology (Eag)mentioning

confidence: 99%

Evidence for intersexual chemical mimicry in a dioecious plant

et al. 2012

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The dioecious Mediterranean fig, Ficus carica, displays a unique phenology in which males sometimes bloom synchronously with females (in summer), and sometimes not (in spring). Ficus carica is engaged in an obligatory mutualism with a specific pollinating wasp, which reproduces only within figs, localising them by their specific scents. We show that scents emitted by male figs show seasonal variation within individual trees. Scents of summer male figs resemble those of the co-flowering females, and are different from those of the same male trees in spring, when female figs are absent. These differences hold even if only compounds electrophysiologically active for pollinators are considered. The similar scents of summer males and females may explain why the rewardless females are still pollinated. These results offer a tractable model for future studies of intersexual chemical mimicry in mutualistic pollination interactions.

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Section: Sensory Tests Using Electrophysiology (Eag)mentioning

confidence: 99%

Evidence for intersexual chemical mimicry in a dioecious plant

et al. 2012

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“…[309] Weitere Beispiele umfassen (AE )-Trihydroxydecipiadien [310] und (+)-Dehydrosolanascon. [306] In Naturstoffen, in denen der Cyclobutanring zentrales Element eines mindestens tricyclischen Skeletts ist, fällt natürlich sofort die intermolekulare [2+2]-Photocycloaddition [312] Spätere Arbeiten umgingen diese Problematik durch Verwendung anderer Alkenkomponenten oder durch temporäre Verknüpfung der Reaktionspartner. [313] Die Spatan-Diterpene (+)-Stoechospermol (239) [314] und (+)-Spatol (240) [315] wurden in analoger Weise synthetisiert.…”

Section: [4+2]-cycloadditionen Von Ortho-chinodimethanenunclassified

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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“…This reaction has also been applied to the synthesis of a number of naturally occurring substances [330][331][332][333][334] and has attracted much attention from the mechanistic viewpoint. [335][336][337] Quinones occupy a very important position in the photoreactions with alkenes in which the conjugated C=C and C=O double bonds competitively take part in the [2+2] photocycloaddition to provide cyclobutane derivatives [338][339][340] and Paterno-Buchi adducts [341][342][343] respectively, depending on the identities of the quinone as well as the alkenes.…”

mentioning

confidence: 99%

Recent advances in 1,4-benzoquinone chemistry

Abraham¹,

Joshi²,

Pardasani³

et al. 2011

J. Braz. Chem. Soc.

170

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As 1,4-benzoquinonas são encontradas em toda a natureza, podendo ser sintetizadas por diversas estratégias. Esta revisão apresenta os desenvolvimentos recentes das metodologias de síntese, das reações de ciclo adição, da química computacional e dos estudos de pulso radiolítico. Destaca ainda a sua significância química e biológica e de seus compostos derivados.1,4-Benzoquinones are ubiquitous in nature and can be synthesized by diverse strategies. Recent developments on their synthetic methodologies, cycloaddition reactions, computational chemistry and pulse radiolytic studies are reported in this review. Their chemical and biological significance as well as their derivates' are also covered.

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The total synthesis of .alpha.- and .beta.-Bourbonene

Cited by 53 publications

References 9 publications

Evidence for intersexual chemical mimicry in a dioecious plant

Evidence for intersexual chemical mimicry in a dioecious plant

Photochemische Reaktionen als Schlüsselschritte in der Naturstoffsynthese

Recent advances in 1,4-benzoquinone chemistry

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