Dolabriferol: A new polypropionate from the skin of the anaspidean mollusc Dolabrifera dolabrifera

Ciavatta, Maria Letizia; Gavagnin, Margherita; Puliti, R.; Cimino, Guido; Martînez, Eugenia; Ortea, Jesús; Mattia, Carlo Andrea

doi:10.1016/0040-4020(96)00764-8

Cited by 45 publications

(35 citation statements)

References 7 publications

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“…2 Dolabriferol ( 1 ), isolated in 1996 by Gavagnin and co-workers from the anaspidean mollusc Dolabrifera dolabrifera , is based on a non-contiguous polypropionate backbone and thus, is considered a prototypical example of this rare class of natural products. 3 After its initial discovery, dolabriferol ( 1 ) quickly became the object of intense scrutiny of organic synthetic chemists. 4 Hitherto, no relevant biological activity data for any member of this interesting class of compounds have been described.…”

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confidence: 99%

“…5 In this paper we report the isolation of dolabriferol ( 1 ) along with two new non-contiguous polypropionate esters, dolabriferol B ( 2 ) 6 and dolabriferol C ( 3 ), 7 whose structures have been proposed on the basis of the interpretation of their spectroscopic data. Taking into account that all attempts by Gavagnin and coworkers to establish the absolute configuration of dolabriferol ( 1 ) by chemical derivatization at C6 failed, 3 with new material in hand, we followed a different approach. Upon measuring the 13 C NMR chemical shift of the carbons adjacent to the secondary alcohol in the presence of chiral lanthanide shift reagents, the absolute configuration at C6 in 1 was found to be R (see Supplementary data).…”

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confidence: 99%

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Dolabriferols B and C, non-contiguous polypropionate esters from the tropical sea hare Dolabrifera dolabrifera

Jiménez-Romero¹,

González²,

Rodrı́guez³

2012

Tetrahedron Letters

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The Caribbean mollusc Dolabrifera dolabrifera from Puerto Rico contains two new propionate-derived metabolites, dolabriferol B and C (2 and 3), in addition to the known compound dolabriferol (1). The structures of dolabriferol B (2) and C (3) were established by comparison of their spectral data with those of 1, and the absolute configuration of 2 was determined from chemical degradation studies. The structure of dolabriferol C (3) was confirmed by X-ray analysis.

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confidence: 99%

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confidence: 99%

Dolabriferols B and C, non-contiguous polypropionate esters from the tropical sea hare Dolabrifera dolabrifera

Jiménez-Romero¹,

González²,

Rodrı́guez³

2012

Tetrahedron Letters

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“…It is thought that this may be a precursor to dolabriferol [34]. The pathway, however, is not obvious.…”

Section: Resultsmentioning

confidence: 90%

Computational assessment of synthetic procedures

Goodman

Socorro

2007

J Comput Aided Mol Des

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Synthetic chemistry is hard because some reasonable looking molecules cannot be made, because there are errors in the chemical literature, because it is easy to miss reaction possibilities and because even the shape of molecules is very difficult to determine. We propose an approach to the computational analysis of reactions that tries to circumvent these difficulties, by restricting the analysis to simple rules for reactivity that can generate a large number of competing pathways. This huge ensemble is filtered using computational methods to pick out the most likely pathways, and to suggest possible products.

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“…Dolabriferol was isolated in 1996, and belongs to a family of non-linear polypropionates [46]. Dolabriferols B and C are closely related structures, and were isolated more recently.…”

Section: Resultsmentioning

confidence: 99%

Reiterative epoxide-based strategies for the synthesis of stereo-n-ads and application to polypropionate synthesis. A personal account

Cruz-Montañez

Morales-Rivera

Torres

et al. 2017

Inorganica Chimica Acta

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The enantioselective synthesis of polypropionates continues to be an attractive realm for the synthetic chemists mostly due to the challenges presented by the number of consecutive stereogenic centers contained within the aliphatic chain. Over the years, our laboratory has developed an epoxide-based three-step reiterative methodology for the construction of these targets, with the ultimate goal that the approach could be extended to the synthesis of polypropionate-containing natural products. The key steps include the diastereoselective epoxidation of allylic and homoallylic alcohols, and the regioselective cleavage of 2-methyl-3,4-epoxy alcohols. The choice of the organometallic reagent, and the cis/trans geometry of the chiral epoxide can be used to control both the relative and absolute configuration of the resulting propionate unit, allowing our approach to be applied in the synthesis of advanced fragments. Additionally, the combination of our first- and second-generation methodologies permits the incorporation of different variations at the methyl moiety.

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Dolabriferol: A new polypropionate from the skin of the anaspidean mollusc Dolabrifera dolabrifera

Cited by 45 publications

References 7 publications

Dolabriferols B and C, non-contiguous polypropionate esters from the tropical sea hare Dolabrifera dolabrifera

Dolabriferols B and C, non-contiguous polypropionate esters from the tropical sea hare Dolabrifera dolabrifera

Computational assessment of synthetic procedures

Reiterative epoxide-based strategies for the synthesis of stereo-n-ads and application to polypropionate synthesis. A personal account

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