Stereoselective Synthesis of 8,9-Licarinediols

Nascimento, Isabele R.; Lopes, Lucia Maria Xavier; Davin, Laurence B.; Lewis, Norman

doi:10.1016/s0040-4020(00)00873-5

Cited by 45 publications

(45 citation statements)

References 13 publications

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“…Whenever Achenbach's results were applied consistently, the wrong configurational assignment was achieved, as was found for 50 51 and (+)-licarin A (51), 23 as well as in the work of Yoshizawa et al 16 The correlation with Achenbach's results could coincidentally lead to the right absolute configuration if one did not take into account the effect of substitution on the ring A. 18,21 Our helicity rule unambiguously confirmed the absolute configuration in these cases.…”

Section: H-nmr Data With That Of the Racemic Cis-2-phenyl-3-methoxycasupporting

confidence: 66%

“…There are numerous publications 16,17,21,23,51 that used the CD results of Achenbach et al 15 for the configurational assignment of isolated neolignans. Whenever Achenbach's results were applied consistently, the wrong configurational assignment was achieved, as was found for 50 51 and (+)-licarin A (51), 23 as well as in the work of Yoshizawa et al 16 The correlation with Achenbach's results could coincidentally lead to the right absolute configuration if one did not take into account the effect of substitution on the ring A.…”

Section: H-nmr Data With That Of the Racemic Cis-2-phenyl-3-methoxycamentioning

confidence: 99%

“…6 The determination of absolute configuration of these biologically active natural products is of great importance to ensure the study of their structure-activity relationship. Besides chemical correlation, 7-9 mainly chiroptical methods (CD and ORD) [10][11][12][13][14][15][16][17][18][19][20][21][22][23] are used to determine their absolute configuration, although chiroptical properties of these chromophore systems have not yet been described in detail. The simple comparison of the measured CD or ORD data may lead to a wrong configurational assignment if one does not carefully choose the appropriate chiroptical rule or the reference compound.…”

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confidence: 99%

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Chiroptical properties of 2,3‐dihydrobenzo[b]furan and chromane chromophores in naturally occurring O‐heterocycles

et al. 2001

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The correlation between the helicity (absolute conformation) of the O-heterocyclic ring of chiral 2,3-dihydrobenzo[b]furan (1) and chromane (2) derivatives and their (1)L(b) band CD was investigated. The same helicity rule was found for both unsubstituted chromophores: P/M helicity of the heterocyclic ring leads to a negative/positive CD within the (1)L(b) band. While the substitution of the fused benzene ring by achiral substituents does not change this helicity rule for the chromane chromophore, it leads to its inversion for the 2,3-dihydrobenzo[b]furan chromophores. On the basis of these observations, the published absolute configurations of natural flavonol and pterocarpan derivatives were confirmed and the configurational assignments of several natural neolignans revised.

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Section: H-nmr Data With That Of the Racemic Cis-2-phenyl-3-methoxycasupporting

confidence: 66%

Section: H-nmr Data With That Of the Racemic Cis-2-phenyl-3-methoxycamentioning

confidence: 99%

mentioning

confidence: 99%

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Chiroptical properties of 2,3‐dihydrobenzo[b]furan and chromane chromophores in naturally occurring O‐heterocycles

et al. 2001

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“…2). The absolute structures of many dihydrobenzo[b]furan-type neolignans have been assigned 21,[40][41][42][43] on the basis of the CD results of Achenbach et al 44) However, Antus et al 45) re- …”

Section: Resultsmentioning

confidence: 99%

Aromatic Constituents from the Heartwood of Santalum album L.

et al. 2005

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“…The various radicals formed are then available to dimerize, and various combinations are possible, with each producing a corresponding dimer. It is interesting to note that when a commercial peroxidase (HRP) is used in in vitro biotransformations, the reaction loses stereoselectivity forming a mixture of isomers 17 . This ambiguous behavior is explained by the action of an auxiliary protein that is present in the natural environment, but absent in the purified commercial enzyme.…”

Section: Biocatalytic Oxidative Coupling Reactionmentioning

confidence: 99%

Formation of bioactive benzofuran via oxidative coupling, using coconut water (Cocos nucifera L.) as biocatalyst

Rodrigues¹,

Barbosa-Filho²,

Marques³

et al. 2017

Org. Commun.

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Abstract:The capacity of simple coconut water, which contains natural peroxidases, to act as a biocatalyst for the oxidative coupling-cyclization of p-(OH)-phenylpropanoids, was evaluated in this work. As a result, dimeric forms of isoeugenol (licarin A) and methyl p-coumarate (methyl dehydrodicoumarate) were obtained. The products of the reactions were characterized by optical rotatory dispersion, and 1 H-NMR and 13 C-NMR spectroscopy. The oxidative coupling-cyclization mechanism for coniferyl alcohol is proposed.

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Stereoselective Synthesis of 8,9-Licarinediols

Cited by 45 publications

References 13 publications

Chiroptical properties of 2,3‐dihydrobenzo[b]furan and chromane chromophores in naturally occurring O‐heterocycles

Chiroptical properties of 2,3‐dihydrobenzo[b]furan and chromane chromophores in naturally occurring O‐heterocycles

Aromatic Constituents from the Heartwood of Santalum album L.

Formation of bioactive benzofuran via oxidative coupling, using coconut water (Cocos nucifera L.) as biocatalyst

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