2020
DOI: 10.1055/s-0039-1690852
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Total Synthesis of Asparenydiol by Two Sonogashira Cross-Coupling Reactions Promoted by Supported Pd and Cu Catalysts

Abstract: Asparenydiol, which is an important natural compound with potential pharmacological activities, was synthesized through two Sonogashira­ cross-coupling reactions catalyzed by supported Pd and Cu catalysts and by a Mitsunobu etherification. The optimization of the Sonogashira­ couplings allowed the use of catalysts supported on different matrices with good results in terms of catalytic efficiency and yields.

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Cited by 5 publications
(3 citation statements)
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“…These organometallic reagents were successfully used in Negishi cross-coupling reactions and showed to be unreactive towards the conjugate addition [13,15]. These considerations, together with our interest in the synthesis of natural products [16][17][18], and our previous results in organozinc halides chemistry [13,15,18,19], prompted us to address our efforts in developing an affordable protocol for the synthesis of chalcones through acylative Negishi cross-coupling, using arylzinc halides prepared by direct insertion [13,[15][16][17][18][19].…”
Section: Resultsmentioning
confidence: 99%
“…These organometallic reagents were successfully used in Negishi cross-coupling reactions and showed to be unreactive towards the conjugate addition [13,15]. These considerations, together with our interest in the synthesis of natural products [16][17][18], and our previous results in organozinc halides chemistry [13,15,18,19], prompted us to address our efforts in developing an affordable protocol for the synthesis of chalcones through acylative Negishi cross-coupling, using arylzinc halides prepared by direct insertion [13,[15][16][17][18][19].…”
Section: Resultsmentioning
confidence: 99%
“…The compounds 1,4-bis(4-aminophenylethynyl)benzene (PN), 1,4-bis(4-thiomethylphenylethynyl)benzene (PS), 1,4-bis(4-ethynylphenylethynyl)benzene (PC), 1,3-bis(4-aminophenylethynyl)benzene (MN), 1,3-bis(4-thiomethylphenylethynyl)benzene (MS), and 1,3-bis(4-ethynylphenylethynyl)benzene (MC) (Fig. 1) were prepared by literature methods 47–50 or minor variations, and characterised as detailed in the ESI †…”
Section: Experimental and Computational Sectionmentioning
confidence: 99%
“…were prepared by literature methods [47][48][49][50] or minor variations, and characterised as detailed in the ESI. †…”
Section: Paper Nanoscalementioning
confidence: 99%