The electrochemical transformations of methyl bicyclohomofarnesoates
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2023-06-30 10:46
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547.057 (5)
Organic chemistry (484)
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LUNGU, Lidia, BLAJA, Svetlana, CIOCARLAN, Alexandru, DRAGALIN, Ion, ARICU, Aculina. The electrochemical transformations of methyl bicyclohomofarnesoates. In: New frontiers in natural product chemistry.: A destiny on the altar of research. Dedicated to academician Pavel Vlad, Ed. 6, 21 mai 2021, Chișinău. Chișinău, Republica Moldova: Tipografia "Artpoligraf", 2021, Ediția 6, p. 15. ISBN 978-9975-3336-7-2. DOI: https://doi.org/10.19261/nfnpc.2021.ab08
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New frontiers in natural product chemistry.
Ediția 6, 2021
Conferința " New frontiers in natural product chemistry."
6, Chișinău, Moldova, 21 mai 2021

The electrochemical transformations of methyl bicyclohomofarnesoates

DOI:https://doi.org/10.19261/nfnpc.2021.ab08
CZU: 547.057

Pag. 15-15

Lungu Lidia, Blaja Svetlana, Ciocarlan Alexandru, Dragalin Ion, Aricu Aculina
 
Institute of Chemistry
 
Proiecte:
 
Disponibil în IBN: 28 mai 2021


Rezumat

Electrochemical transformations have attracted much attention in synthetic organic chemistry, because they are cheap and environmentally friendly. Nowadays the interest for homodrimanic compounds increases substantially and frequently their syntheses were performed starting from known methyl bicyclohomofarnesoates 1-3, which was obtained from commercially available (+)-sclareolide [1]. Methyl esters 1-3 were subjected to anodic oxidation in presence of lithium perchlorate as a supporting electrolyte. Additionally to previously reported compounds 4 and 5 [2], a series of minor compounds 6-9 were isolated from the reaction mixture and characterized [1]. The electrochemical oxidation of esters 1-3 depends significantly on the reaction conditions, in particular, on the supporting electrolyte and the solvent. In the case when the anodic oxidation of methyl esters 1-3 were performed in a mixture of AcOH-Ac2O (5:1) and presence of AcONa, the products 4, 10-13 were obtained in depicted yields (Scheme). The structures of all synthesized compounds were fully confirmed by spectral methods of analysis (IR, 1H and 13C NMR and GS-MS). Reagents and conditions: a. LiClO4, MeOH, ē, 5h; b. AcONa, Ac2O, AcOH glac., ē, 5h. Scheme The above examples confirm that electrochemical transformations are a suitable alternative for the synthesis of terpene compounds by processes belonging to the field of "green chemistry".