Asymmetric dihydroxylation of drim-7-en-11-ol: Synthesis of diastereomerically pure driman-7α,8α,11-triol and its elaboration into novel chlorinated norlabdanic compounds
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VLAD, Pavel, GORINCIOI, Elena, ARICU, Aculina, BARBA, Alic, MANZOCCHI, Ada, SANTANIELLO, Enzo. Asymmetric dihydroxylation of drim-7-en-11-ol: Synthesis of diastereomerically pure driman-7α,8α,11-triol and its elaboration into novel chlorinated norlabdanic compounds. In: Tetrahedron Asymmetry, 2010, vol. 21, nr. 17, pp. 2108-2116. ISSN 0957-4166. DOI: https://doi.org/10.1016/j.tetasy.2010.06.029
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Tetrahedron Asymmetry
Volumul 21, Numărul 17 / 2010 / ISSN 0957-4166 /ISSNe 1362-511X

Asymmetric dihydroxylation of drim-7-en-11-ol: Synthesis of diastereomerically pure driman-7α,8α,11-triol and its elaboration into novel chlorinated norlabdanic compounds

DOI:https://doi.org/10.1016/j.tetasy.2010.06.029

Pag. 2108-2116

Vlad Pavel1, Gorincioi Elena1, Aricu Aculina1, Barba Alic1, Manzocchi Ada2, Santaniello Enzo2
 
1 Institute of Chemistry of the Academy of Sciences of Moldova,
2 University of Milan
 
 
Disponibil în IBN: 15 mai 2023


Rezumat

The asymmetric dihydroxylation of drim-7-en-11-ol was studied in detail and diastereomerically pure driman-7α,8α,11- and driman-7β, 8β,11-triols were prepared. Further elaboration of driman-7α, 8α,11-triol afforded 14,15-bisnorlabd-7α,8α- isopropylidenedioxy-11,13-dione from which a novel chlorinated bisnorlabdanic compound (14,15-bisnorlabd-12-ene-12-chloro-8α,13-epoxy-7α-ol-11- one) and an unusual dichloro-derivative, 13,14,15,16-tetranorlabd-12-dichloro- 7α-acetoxy-8α-ol-11-one, were obtained.

Cuvinte-cheie
13, 14, 15, 16 tetranorlabd 12 dichloro 7alpha acetoxy 8alpha ol 11 one, 14, 15 bisnorlabd 12 ene 12 chloro 8alpha, 13 epoxy 7alapha ol 11 one, diterpene, drim 7 en 11 ol, driman 7alpha, 8alpha, 11 triol, unclassified drug