LTA‐mediated synthesis and complete assignment of <sup>1</sup>H and <sup>13</sup>C NMR data of two natural 11‐nordrimanes: isonordrimenone and polygonone

Moreno‐Osorio, Luis; Espinoza, Luis; Cuéllar, Mauricio; Preite, Marcelo D.

doi:10.1002/mrc.2067

Cited by 3 publications

(4 citation statements)

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“…On the other hand, the unsaturated ketone 16 was obtained by treating 3 with the oxidation reagent pyridinium chlorochromate (PCC) [ 14 ]. Their structures were determined by comparison with the previously reported data [ 14 , 22 , 23 ]. In addition, catalytic hydrogenation of 3 using Pd/C (10% Pd), led to the saturated drimanol 17 whose spectroscopic data were in accordance to the literature [ 24 ].…”

Section: Resultsmentioning

confidence: 99%

Structural Requirements for the Antifungal Activities of Natural Drimane Sesquiterpenes and Analogues, Supported by Conformational and Electronic Studies

et al. 2013

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Seventeen drimanes including polygodial (1), isopolygodial (2), drimenol (3) and confertifolin (4) obtained from natural sources and the semi-synthetic derivatives 5–17 obtained from 1–3, were evaluated in vitro for antifungal properties against a unique panel of fungi with standardized procedures by using two end-points, MIC100 and MIC50. A SAR analysis of the whole series, supported by conformational and electronic studies, allowed us to show that the Δ7,8 -double bond would be one of the key structural features related to the antifungal activity. The MEPs obtained for active compounds exhibit a clear negative minimum value (deep red zone) in the vicinity of the Δ7,8 -double bond, which is not present in the inactive ones. Apart of this negative zone, a positive region (deep blue) appears in 1, which is not observed either in its epimer 2 nor in the rest of the active compounds. The LogP of active compounds varies between 2.33 and 3.84, but differences in MICs are not correlated with concomitant variations in LogP values.

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Section: Resultsmentioning

confidence: 99%

Structural Requirements for the Antifungal Activities of Natural Drimane Sesquiterpenes and Analogues, Supported by Conformational and Electronic Studies

et al. 2013

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“…41 Isonordrimenone and polygonone have been synthesized and their 1 H and 13 C NMR-spectra unambiguously assigned. 42 Syntheses of 1-(R)-hydroxypolygodial, 1-(R)-hydroxyisotadeonal, 43 (+)-austrodoral and (+)-austrodoric acid have achieved. 44 The elimination of the C-8 functional groups from driman-8a,11-diol 11-monoacetate and its diacetate has been studied.…”

Section: Bicyclofarnesanementioning

confidence: 99%

Natural sesquiterpenoids

Fraga

2008

Nat. Prod. Rep.

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“…The solvent was concentrated under vacuum to afford crude reaction, and then it was purified through column chromatography using hexane:acetate 8:2 as mobile phase. The NMR signals (see Appendix A) were compared with previous reports [28][29][30].…”

Section: Synthesis Of Driman-11-ol (2)mentioning

confidence: 99%

“…In chlorine as a substituent, the inductive effect predominates, behaving as an electro-attractor. The structural determination of reaction intermediaries 2 and 3 was performed by comparing 1 H NMR and 13 C NMR spectra with previous reports [28][29][30][31]. The analysis of compounds 4-15 was centered on the 1 H NMR and 13 C NMR signals of the aromatic ring and the GC-MS data because the signals of the decalinic ring did not vary (see Section 2.2.4).…”

Section: The Effect On Mycelial Growthmentioning

confidence: 99%

Characterization of the Fungitoxic Activity on Botrytis cinerea of N-phenyl-driman-9-carboxamides

Melo

Armstrong

Navarro

et al. 2021

JoF

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A total of 12 compounds were synthesized from the natural sesquiterpene (-) drimenol (compounds 4 to 15). The synthesized compounds corresponded to N-phenyl-driman-9-carboxamide derivatives, similar to some fungicides that inhibit the electron-transport chain. Their structures were characterized and confirmed by 1H NMR, 13C NMR spectroscopy, and mass spectrometry. Compounds 5 to 15 corresponded to novel compounds. The effect of the compounds on the mycelial growth of Botrytis cinerea was evaluated. Methoxylated and chlorinated compounds in the aromatic ring (compounds 6, 7, 12, and 13) exhibited the highest antifungal activity with IC50 values between 0.20 and 0.26 mM. On the other hand, the effect on conidial germination of B. cinerea of one methoxylated compound (6) and one chlorinated compound (7) was analyzed, and no inhibition was observed. Additionally, compound 7 decreased 36% the rate of oxygen consumption by germinating conidia.

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LTA‐mediated synthesis and complete assignment of ¹H and ¹³C NMR data of two natural 11‐nordrimanes: isonordrimenone and polygonone

Abstract: Two naturally occurring 11-nordrimanes were synthesized, and their (1)H and (13)C NMR spectra were unambiguously assigned in full for the first time.

Cited by 3 publications

References 18 publications

Structural Requirements for the Antifungal Activities of Natural Drimane Sesquiterpenes and Analogues, Supported by Conformational and Electronic Studies

Structural Requirements for the Antifungal Activities of Natural Drimane Sesquiterpenes and Analogues, Supported by Conformational and Electronic Studies

Natural sesquiterpenoids

Characterization of the Fungitoxic Activity on Botrytis cinerea of N-phenyl-driman-9-carboxamides

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LTA‐mediated synthesis and complete assignment of 1H and 13C NMR data of two natural 11‐nordrimanes: isonordrimenone and polygonone

Abstract: Two naturally occurring 11-nordrimanes were synthesized, and their (1)H and (13)C NMR spectra were unambiguously assigned in full for the first time.

Cited by 3 publications

References 18 publications

Structural Requirements for the Antifungal Activities of Natural Drimane Sesquiterpenes and Analogues, Supported by Conformational and Electronic Studies

Structural Requirements for the Antifungal Activities of Natural Drimane Sesquiterpenes and Analogues, Supported by Conformational and Electronic Studies

Natural sesquiterpenoids

Characterization of the Fungitoxic Activity on Botrytis cinerea of N-phenyl-driman-9-carboxamides

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Product

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LTA‐mediated synthesis and complete assignment of ¹H and ¹³C NMR data of two natural 11‐nordrimanes: isonordrimenone and polygonone