916514-80-2Relevant academic research and scientific papers
Asymmetric total synthesis of (+)- and (-)-clusianone and (+)- and (-)-clusianone methyl enol ether via ACC alkylation and evaluation of their anti-HIV activity
Garnsey, Michelle R.,Matous, James A.,Kwiek, Jesse J.,Coltart, Don M.
supporting information; experimental part, p. 2406 - 2409 (2011/06/17)
The total asymmetric synthesis of (+)- and (-)-clusianone and (+)- and (-)-clusianone methyl enol ether is reported. Asymmetric induction is achieved through the use of ACC alkylation, providing the key intermediates with an er of 99:1. The four synthetic
Development of a strategy for the asymmetric synthesis of polycyclic polyprenylated acylphloroglucinols via N-amino cyclic carbamate hydrazones: Application to the total synthesis of (+)-clusianone
Garnsey, Michelle R.,Lim, Daniel,Yost, Julianne M.,Coltart, Don M.
supporting information; experimental part, p. 5234 - 5237 (2011/02/23)
A broadly applicable asymmetric synthetic strategy utilizing N-amino cyclic carbamate alkylation that provides access to the various stereochemical permutations of a common structural motif found in many polycyclic polyprenylated acylphloroglucinols is de
α,α′-annulation of 2,6-prenyl-substituted cyclohexanone derivatives with malonyl chloride: Application to a short synthesis of (±)-clusianone. Formation and rearrangement of a biogenetic-like intermediate
Nuhant, Philippe,David, Marc,Pouplin, Thomas,Delpech, Bernard,Marazano, Christian
, p. 287 - 289 (2007/10/03)
(Chemical Equation Presented) Conditions were found for the successful Effenberger α,α′-annulation of 3,3-dimethyl-2,4,6-triprenyl cyclohexanone silyl enol ethers with malonyl chloride to give the corresponding bicyclo[3.3.1]nonane-trione in 35% yield, th
Synthesis of polyprenylated acylphloroglucinols using bridgehead lithiation: The total synthesis of racemic clusianone and a formal synthesis of racemic garsubellin A
Ahmad, Nadia M.,Rodeschini, Vincent,Simpkins, Nigel S.,Ward, Simon E.,Blake, Alexander J.
, p. 4803 - 4815 (2008/02/05)
(Chemical Equation Presented) The synthesis of polyprenylated phloroglucinol natural products, including clusianone, nemorosone, and garsubellin A, was pursued by a strategy involving construction of a core bicyclo[3.3.1]nonanetrione structure and subsequent elaboration via organolithium intermediates. Appropriate bridged core structures were obtained through the cyclization of a suitably substituted cyclohexanone enol ether or enol silane with malonyl dichloride. Additional substituents were then introduced by means of regioselective lithiation reactions, including the generation of bridgehead enolates, thus enabling the total synthesis of clusianone and also of an advanced intermediate toward nemorosone. In the case of garsubellin A, an additional THF-like ring was elaborated by a biomimetic 5-exo-tet cyclization of an enol ether (or enol) with a side-chain epoxide. This enabled a formal synthesis of racemic garsubellin A by accessing one of the late intermediates in the Danishefsky synthesis.
Synthesis of (+/-)-clusianone: High-yielding bridgehead and diketone substitutions by regioselective lithiation of enol ether derivatives of bicyclo[3.3.1]nonane-2,4,9-triones
Rodeschini, Vincent,Ahmad, Nadia M.,Simpkins, Nigel S.
, p. 5283 - 5285 (2007/10/03)
A concise synthesis of the polyprenylated acylphloroglucinol natural product, clusianone, in racemic form, is described. An Effenburger cyclization generated a core bicyclo[3.3.1]nonane-trione structure, which was then elaborated by means of regioselectiv
