6-[ω-arylalkenyl]-5,6-dihydro-α-pyrones from Cryptocarya moschata (Lauraceae)

Cavalheiro, Alberto José; Yoshida, Massayoshi

doi:10.1016/s0031-9422(99)00532-4

Cited by 98 publications

(125 citation statements)

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“…In 2010, Cavalheiro and Yoshida 21 isolated eleven structurally related 6-[ω-arylalkenyl]-5,6-dihydro-α-pyrones from the branch and steam bark of Cryptocarya moschata, a Brazilian tree, and named them cryptomoscatones D2, E1, E2, E3 and F1, and cryptopyranmoscatones A1, A2, A3, B1, B2 and B4. The structures of all these compounds were established by standard spectroscopic methods.…”

Section: Cryptomoscatone E3mentioning

confidence: 99%

“…In addition to this contradiction, the connection between the two stereoclusters configuration of the molecule (the C-8/C-12 stereotriad and C-6 of the lactone) could not be carried out. 21 As part of an ongoing interest in the total synthesis and structural elucidation of natural products bearing the 5,6-dihydropyran-2-one motif, 22 Pilli and co-workers 23 tackled the cryptomoscatone E3 case. Given the inconsistencies discussed above regarding the structure of the natural product, and in order to avoid the synthesis of all plausible isomers, a computer-guided total synthesis approach was conducted.…”

Section: Cryptomoscatone E3mentioning

confidence: 99%

See 1 more Smart Citation

Computer-Guided Total Synthesis of Natural Products. Recent Examples and Future Perspectives

Della‐Felice¹,

Pilli²,

Sarotti³

2018

J. Braz. Chem. Soc.

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Quantum chemical calculations of nuclear magnetic resonance (NMR) shifts and coupling constants have been extensively employed in recent years mainly to facilitate structural elucidation of organic molecules. When the results of such calculations are used to determine the most likely structure of a natural product in advance, guiding the subsequent synthetic work, the term "computer-guided synthesis" could be coined. This review article describes the most relevant examples from recent literature, highlighting the scope and limitations of this merged computational/experimental approach as well.

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Section: Cryptomoscatone E3mentioning

confidence: 99%

Section: Cryptomoscatone E3mentioning

confidence: 99%

Computer-Guided Total Synthesis of Natural Products. Recent Examples and Future Perspectives

Della‐Felice¹,

Pilli²,

Sarotti³

2018

J. Braz. Chem. Soc.

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“…The chromosome number is 2n = 24 (Moraes & Gardingo 1996). This species is rich in alkaloids, styryllpyrones, and flavonoids (Cavalheiro & Yoshida 2000). Its bark, bitter and scented, is considered to be stomachical and helpful in fighting colic and diarrhea, in folk medicine (Vattimo 1957).…”

Section: Cryptocarya Moschata Neesmentioning

confidence: 99%

Genetic structure of natural populations of Cryptocarya moschata Nees (Lauraceae) from southeastern Brazilian Atlantic rain forest

Moraes

Derbyshire²

2004

Biota Neotrop.

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This study was accomplished on a more comprehensive basis to evaluate previous questions that were raised from a preliminary article about the genetic structure of Cryptocarya moschata populations. Thus, through the analysis of 40 polymorphic allozyme loci, allele frequencies were estimated from 335 individuals of 11 natural populations of C. moschata from six hydrographic basins of São Paulo state and Serra da Estrela, Rio de Janeiro, Brazil. Estimates of Wright's F statistics were done through the analysis of variance, presenting average values of <img border=0 width=32 height=32 id="_x0000_i1026" src="../../../../../../img/revistas/bn/v4n1/img/a04car(f).jpg" align=absmiddle > or = 0.352, <img border=0 width=32 height=32 id="_x0000_i1027" src="../../../../../../img/revistas/bn/v4n1/img/a04car(0p).jpg" align=absmiddle > or = 0.285 and <img border=0 width=32 height=32 id="_x0000_i1028" src="../../../../../../img/revistas/bn/v4n1/img/a04car(f2).jpg" align=absmiddle > or = 0.097. These results indicated that individuals within populations must be panmitic, and that the diversity among populations is fairly high, being superior to what would be expected for groups of plants having a full-sib family structure. From estimates of <img border=0 width=32 height=32 id="_x0000_i1029" src="../../../../../../img/revistas/bn/v4n1/img/a04car(0p).jpg" align=absmiddle>obtained for populations taken two at a time, the model of isolation by distance was tested; data did not fit the model, showing that <img border=0 width=32 height=32 id="_x0000_i1030" src="../../../../../../img/revistas/bn/v4n1/img/a04car(0p).jpg" align=absmiddle>did not increase by the respective increasing of the geographic distance. The estimated gene flow of 0.55 migrants per generation corroborated the pronounced populational differentiation, indicating that drift effects should be more important than the selection ones. The effective population sizes found from the sampled populations showed that there was an adequate genetic representativeness of the samples for those with relatively low values of <img border=0 width=32 height=32 id="_x0000_i1031" src="../../../../../../img/revistas/bn/v4n1/img/a04car(f2).jpg" align=absmiddle>. Though, under a metapopulation context, the effective population size was 17.07 individuals, indicating that sampling performed for the species corresponded to 88.44% of the maximum effective size obtained from 11 populations with a <img border=0 width=32 height=32 id="_x0000_i1032" src="../../../../../../img/revistas/bn/v4n1/img/a04car(0p).jpg" align=absmiddle>of 0.285, equivalent to only 5.09% individuals for the total sampled. Management and conservation strategies aimed at preserving high intrapopulation genetic variation in C. moschata would imply in the maintenance of populations with great number of individuals. Moreover, for the preservation of the species as a whole, the maintenance of many such populations would be mandatorily recommended, which denotes that the conservation of large areas of Atlantic rain forest should be necessary to hold its evolutionary dynamics.

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“…1 Among these compounds, we highlight Cryptomoscatone D1 and D2, isolated from C. mandiocanna, 2 for which a definitive proof of structure is still lacking. In this work, we describe our synthetic efforts toward compounds 1 and 2 in order to contribute to the elucidation of the stereochemistry of Criptomoscatones D1 and D2 ( Figure 1).…”

Section: Introductionmentioning

confidence: 99%

Synthetic studies towards the elucidation of the stereochemistry of compounds of the Cryptomoscatone D family

Drekener¹,

Pilli²

2013

Proceedings of the 14th Brazilian Meeting on Organic Synthesis Proceedings

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6-[ω-arylalkenyl]-5,6-dihydro-α-pyrones from Cryptocarya moschata (Lauraceae)

Cited by 98 publications

References 10 publications

Computer-Guided Total Synthesis of Natural Products. Recent Examples and Future Perspectives

Computer-Guided Total Synthesis of Natural Products. Recent Examples and Future Perspectives

Genetic structure of natural populations of Cryptocarya moschata Nees (Lauraceae) from southeastern Brazilian Atlantic rain forest

Synthetic studies towards the elucidation of the stereochemistry of compounds of the Cryptomoscatone D family

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