Synthesis of some guanidine diterpenoids
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GRINCO, Marina, GÎRBU, Vladilena, PRUTEANU, Elena, MORĂRESCU (CHETRARU), Olga, KULCIŢKI, Veaceslav, UNGUR, Nikon. Synthesis of some guanidine diterpenoids. In: Achievements and perspectives of modern chemistry, 9-11 octombrie 2019, Chişinău. Chisinau, Republic of Moldova: Tipografia Academiei de Ştiinţe a Moldovei, 2019, p. 222. ISBN 978-9975-62-428-2.
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Achievements and perspectives of modern chemistry 2019
Conferința "International Conference "Achievements and perspectives of modern chemistry""
Chişinău, Moldova, 9-11 octombrie 2019

Synthesis of some guanidine diterpenoids


Pag. 222-222

Grinco Marina, Gîrbu Vladilena, Pruteanu Elena, Morărescu (Chetraru) Olga, Kulciţki Veaceslav, Ungur Nikon
 
Institute of Chemistry
 
Disponibil în IBN: 11 noiembrie 2019


Rezumat

Guanidine compounds represent a large group of biologically active secondary metabolites [1, 2]. Several of them, despite their low content in the source, have been intensively explored as new promising agents against various cancer cell lines [3, 4] and in the infectious diseases treatment [5]. Taking into consideration all the data explored in the literature it seemed attractive and necessary to synthesize guanidine containing diterpenoids and to study their biological activity. In this communication we present convenient approaches for the synthesis of some polycyclic nitrogen containing diterpenoids, starting with accessible (-)-sclareol (1) and ent-kaur16-en-19-oic acid (2), according to the scheme given below.formulaReagents and conditions:(a) Senecioic acid, NMP, CMPI, 2 h, then (3), NMP, DIEA, 52%, (b) H2, Pd/C, 1,3-diboc2-(trifluoromethylsulfonyl)guanidine, EtOAc, 98%; (c) TFA/DCM, 95%. Scheme As result, a series of guanidine diterpenoids, N-labd-8(9),13(E)-dien-15-oyl guanidine (3), N-labd-8(9),13(E)-dien-15-oyl-N'-senecioyl guanidine (4) and metil-(16R)-17-guanidin-entkauran19-oat (6), were obtained. All compounds were characterized by NMR spectroscopy.