Mollecular rearrangements in the synthesis of bioactive terpenoids with new carbon skeletons
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2021-11-08 16:27
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547.597.057:577.1:615.1 (1)
Chimie organică (475)
Bazele materiale ale vieții. Biochimie. Biologie moleculară. Biofizică (655)
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UNGUR, Nikon, KULCIŢKI, Veaceslav. Mollecular rearrangements in the synthesis of bioactive terpenoids with new carbon skeletons. 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. 18. ISBN 978-9975-3336-7-2. DOI: https://doi.org/10.19261/nfnpc.2021.ab11
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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

Mollecular rearrangements in the synthesis of bioactive terpenoids with new carbon skeletons

DOI: https://doi.org/10.19261/nfnpc.2021.ab11
CZU: 547.597.057:577.1:615.1

Pag. 18-18

Ungur Nikon, Kulciţki Veaceslav
 
Institute of Chemistry
 
Proiect:
20.80009.8007.03 Noi substanțe cu potențial preventiv și terapeutic în baza compușilor naturali de origine vegetală și a matodelor moderne de sinteză organică
 
Disponibil în IBN: 28 mai 2021


Rezumat

Diterpenoids represent one of the most numerous and important classes of natural terpenoids, both from theoretical and practical point of view. These are widespread all over the earth, including microorganisms and lower plants, aquatic and terrestrial organisms [1,2]. Many representatives have found vast applications in pharmaceutical industry, perfumery and cosmetics, as well as in food production. An important path for accessing policyclic diterpenoids is represented by molecular rearrangements under the action of electrophilic agents, including both conventional and Lewis acids and also superacids. Molecular rearrangements of cyclic diterpenoids lead as a rule to diterpenic compounds with modified skeletons, including unprecedented ones. Basing on such strategies, a series of work has been demonstrated, leading to molecular rearrangements of a series of natural diterpenoids, such as ent-kaur-16-en-19-oic (1) and enttrachiloban19-oic (2) acids [3], as well as phillocladan-16-ol (3) [4], (1R,2S,7S,10S,12S)2,6,6,12,12-pentamethyl-tetracyclo[10.2.1.01,10.02,7]-eicosan-11-ol (4) [5], hiban-14 -ol (5) [6], methyl 12-hidroxi-ent-isocopal-13(16)-en-15-oate (6) [7] and (5S,8R,9S,10S)-8,9-epoxi12-acetoxybiciclohomofarnesane (7) [8,9] – diterpenoids obtained synthetically from (-)sclareol (9). The possible mechanisms for the formation of new structures resulting from molecular rearrangement reactions have been hypothesized.