2009
DOI: 10.1002/chem.200901675
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Total Synthesis and Biological Evaluation of (+)‐Neopeltolide and Its Analogues

Abstract: The stereocontrolled total synthesis of the originally proposed (1) and correct (2) structures of (+)-neopeltolide, a novel marine macrolide natural product with highly potent antiproliferative activity against several cancer cell lines as well as potent antifungal activity, has been achieved by exploiting a newly developed Suzuki-Miyaura coupling/ring-closing metathesis strategy. Alkylborate 44, which was generated in situ from iodide 34, was coupled with enol phosphate 8 by a Suzuki-Miyaura coupling. Ring-cl… Show more

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Cited by 65 publications
(34 citation statements)
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“…Biological evaluation of synthetic (À À)-lyngbyaloside Band related compounds Evaluation of the antiproliferative activity of the proposed structure 1,t he correct structure 86 and its aglycon 102,a nd (À)-13-demethyllyngbyaloside B( 5)a gainst as mallp anel of human cancer cell lines was carried out by using WST-8 assay (Figure 3). [67,68] The aglycon 102 was preparedf rom 99 by hydrolysis of the silyl ether and methyl acetal( Scheme 16). In contrastt ow hat was reportedb yM oore et al,w ew ere surprised to find that the correct structure 86 was almosti nactive against KB cells and the proposed structure 1 was also essentially inactive.T hese compounds also did not show appreciable activity in human non-smallc ell lung adenocarcinoma A549 cells;however,moderate antiproliferative activity was observed in human promyelocytic leukemia HL-60 cells and human Burkitt lymphoma DAUDI cells.…”
Section: Resultsmentioning
confidence: 99%
“…Biological evaluation of synthetic (À À)-lyngbyaloside Band related compounds Evaluation of the antiproliferative activity of the proposed structure 1,t he correct structure 86 and its aglycon 102,a nd (À)-13-demethyllyngbyaloside B( 5)a gainst as mallp anel of human cancer cell lines was carried out by using WST-8 assay (Figure 3). [67,68] The aglycon 102 was preparedf rom 99 by hydrolysis of the silyl ether and methyl acetal( Scheme 16). In contrastt ow hat was reportedb yM oore et al,w ew ere surprised to find that the correct structure 86 was almosti nactive against KB cells and the proposed structure 1 was also essentially inactive.T hese compounds also did not show appreciable activity in human non-smallc ell lung adenocarcinoma A549 cells;however,moderate antiproliferative activity was observed in human promyelocytic leukemia HL-60 cells and human Burkitt lymphoma DAUDI cells.…”
Section: Resultsmentioning
confidence: 99%
“…Our synthesis of the macrocyclic core began from the known 12 chiral alcohol 6 . As shown in Scheme 1, treatment of allyl alcohol 6 with acryloyl chloride and Et 3 N gave diene 11 , which was subjected to ring closing metathesis using the Grubbs II catalyst to give α , β -unsaturated lactone 12 .…”
mentioning
confidence: 99%
“…Providing a reliable protocol for the formation of aryl-aryl bonds, it has stimulated great progress in modern material [1][2][3][4] and medicinal chemistry. [5][6][7][8][9][10][11] Accordingly, there is sustained interest in developing Pd catalysts that can offer the requisite reactivity with high TON and TOF. To this end, a number of ligands were developed, which can generate highly active catalysts with wider scope, [12][13][14] allowing these processes to be viable on an industrial scale.…”
Section: Introductionmentioning
confidence: 99%