The first synthesis of spirocyclopentyl derivatives of lupane triterpenoids by radical nitrocyclization of C-2-diallyl substituted betulonates

Radical cyclization of the 1,6-hexadiene moiety in 2,2-diallyl substituted methyl or benzyl dihydrobetulonates initiated by Fe(NO3)3·9H2O in the presence of FeCl3 or LiCl gave hitherto unknown spirocyclic compounds in which ring A of the lupane triterpenoid at position C-2 is spiro coupled with a vi...

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Bibliographic Details
Published in:Tetrahedron letters 2012-01, Vol.53 (2), p.217-221
Main Authors: Spivak, Anna Yu, Shakurova, Elvira R., Nedopekina, Darya A., Khursan, Sergey L., Ovchinnikov, Michail Yu, Khalilov, Leonard M., Odinokov, Victor N.
Format: Article
Language:English
Subjects:
1,6-Hexadienes
Assessments
Betulonic acid
Derivatives
Joining
Lupane triterpenoids
Nuclear power generation
Quantum chemistry
Radical cyclization
Radicals
Spirocycles
Synthesis
Tetrahedrons
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Summary:Radical cyclization of the 1,6-hexadiene moiety in 2,2-diallyl substituted methyl or benzyl dihydrobetulonates initiated by Fe(NO3)3·9H2O in the presence of FeCl3 or LiCl gave hitherto unknown spirocyclic compounds in which ring A of the lupane triterpenoid at position C-2 is spiro coupled with a vicinally substituted nitromethyl- and chloromethylcyclopentane. Based on a quantum-chemical assessment of the energy characteristics of this reaction, the most probable configurations of the chiral atoms in the spirocyclopentane ring were determined for the major diastereomers isolated in individual form.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2011.11.020