Studies on the Synthesis of Scoparic Acid A and Related Labdane Diterpenoids. Synthesis of (E)-6β-Hydroxylabda-8-(17),13-dien-15-oic Acid

Abad, Antonio; Arnó, Manuel; Agulló, Consuelo; Cuñat, Ana C.; Meseguer, Benjamin; Zaragozá, Ramón J.

doi:10.1021/np50102a016

Cited by 10 publications

(3 citation statements)

References 17 publications

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“…(−)- ent -6-β-Hydroxycopalic acid (7) was obtained as a colorless oil: [α] D 25 −25.3 ( c 0.43, CHCl 3 ); 1 H NMR and 13 C NMR data were consistent with those previously reported and authentic sample , ; ESI-MS, m / z 321 [M + H] + .…”

Section: Methodssupporting

confidence: 78%

“…Together with lignans 1 and 2, (-)-copalic acid ( 5), (-)fargesin ( 6), (-)-ent-6-β-hydroxy-copalic acid (7), (8R,8′R,9R)and (8R,8′R,9S)-cubebins ( 8), (-)-phillygenin (9), and 2-oxokolavenic acid (10) were isolated from the hexane extract of the leaves by partition and chromatographic procedures. The structures of these compounds were identified by comparison of their spectroscopic data (ESI-MS, IR, 1 H and 13 C NMR) and optical activities (R D ) with those reported in the literature (21,22,(24)(25)(26)(27)(28)(29)(30)(31)(32). Although furofuran lignans have been known for some time, the determination of their configurations is still a subject of controversy (26,27).…”

Section: Resultsmentioning

confidence: 99%

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Evaluation of Insecticidal Activity of Diterpenes and Lignans from Aristolochia malmeana against Anticarsia gemmatalis

Messiano

Vieira

Machado

et al. 2008

J. Agric. Food Chem.

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The insecticidal activity of hexane extracts from the roots and leaves of Aristolochia malmeana was evaluated against Anticarsia gemmatalis larvae by topical application. Extract from the roots was the most active and caused 50% mortality in larvae at 308.4 microg/microL. From this extract, a clerodane diterpene, (-)-kolavenic acid, and three lignans, (-)-kusunokinin, (-)-hinokinin, and (8 S,8' R,9 S)-cubebin, were isolated by chromatography and partition procedures and then evaluated for their insecticidal activities either individually or in pairs. (-)-Kusunokinin showed higher activity against A. gemmatalis (LD10=9.3, LD50=230.1 microg/microL) than the crude extract, and its activity was dose-dependent, whereas the other constituents did not exhibit any significant activity. Together with (-)-kusunokinin and (-)-hinokinin, (-)-copalic acid, (-)-2-oxokolavenic acid, (-)- ent-6-beta-hydroxy-copalic acid, (8 R,8' R,9 R)- and (8 R,8' R,9 S)-cubebins, (-)-fargesin, and (-)-phillygenin were isolated from the hexane extract of the leaves. The compounds were identified on the basis of spectroscopic analysis.

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Section: Methodssupporting

confidence: 78%

Section: Resultsmentioning

confidence: 99%

Evaluation of Insecticidal Activity of Diterpenes and Lignans from Aristolochia malmeana against Anticarsia gemmatalis

Messiano

Vieira

Machado

et al. 2008

J. Agric. Food Chem.

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“…Workup as in the case of 1 gave a residue which was purified by cc over Si gel. The fractions eluted with hexane-EtOAc (8:2) afforded diacetate 7 as a white solid which was recrystallized from CHCl3/hexane to yield white prisms (97 mg, 73%), mp 128-130°; Arteag-9-en-7a,8$-diol-1 -one 7-monoacetate [8],-A solution of endiolone 3 (83 mg) in pyridine (1 ml) was treated with Ac20 (1 ml). The reaction mixture was heated on a steam bath for 90 min, poured over ice-H20, and extracted with EtOAc.…”

Section: T H I S C O N T E N T Imentioning

confidence: 99%

Molecular Rearrangement of Rastevione Mesylate into Arteagane Derivatives

Román¹,

Zepeda²,

Morales³

et al. 1995

J. Nat. Prod.

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Molecular rearrangment of rastevione mesylate {!] in alkaline medium afforded two epimeric 2,6,6,11 -tetramethyltricyclo[5.4.0.04,8]undecane derivatives [2 and 3] by a 1,3-bond migration. Their stereostructures, which possess a new hydrocarbon skeleton named arteagane, were elucidated from nmr data in combination with X-ray diffraction analyses of 3 and its diacetate 7. The conformations of 2, 3, and several derivatives are reported.Molecular rearrangements of natural products offer the possibility of generating substances with novel skeletons (1-3) and increased understanding of their chemical behavior (4-6), which can be applied to synthetic approaches (7,8). In continuation of our research on molecular rearrangements of sesquiterpenes (9,10), we report herein the transformation of the longi^inene derivative rastevione mesylate [1] to the 2,6,6,11tetramethyltricyclo[5.4.0.0 ' Jundecane derivatives 2 and 3 by a 1,3-bond migration.

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Eschenmoser Fragmentation

2010

Comprehensive Organic Name Reactions and Reagents

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The cleavage of α,β‐epoxyketones under mild conditions to acetylenic aldehydes or ketones with p ‐toluenesulfonylhydrazine using pyridine, NaHCO 3 , or Na 2 CO 3 as a catalyst is generally referred to as the Eschenmoser fragmentation. The p ‐toluenesulfonylhydrazine is not a suitable reagent for this reaction; therefore, alternative sulfonylhydrazines have been applied to this reaction, including p ‐nitrobenzenesulfonylhydrazine. This reaction provides an alternative and spectacular type of ring expansion for the cyclic ketones.

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Studies on the Synthesis of Scoparic Acid A and Related Labdane Diterpenoids. Synthesis of (E)-6β-Hydroxylabda-8-(17),13-dien-15-oic Acid

Cited by 10 publications

References 17 publications

Evaluation of Insecticidal Activity of Diterpenes and Lignans from Aristolochia malmeana against Anticarsia gemmatalis

Evaluation of Insecticidal Activity of Diterpenes and Lignans from Aristolochia malmeana against Anticarsia gemmatalis

Molecular Rearrangement of Rastevione Mesylate into Arteagane Derivatives

Eschenmoser Fragmentation

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