423764-66-3Relevant academic research and scientific papers
Highly potent activity of (1R,2R,6S)-3-methyl-6-(prop-1-en-2-yl)cyclohex-3- ene-1,2-diol in animal models of parkinson's disease
Ardashov, Oleg V.,Pavlova, Alla V.,Il'ina, Irina V.,Morozova, Ekaterina A.,Korchagina, Dina V.,Karpova, Elena V.,Volcho, Konstantin P.,Tolstikova, Tat'yana G.,Salakhutdinov, Nariman F.
, p. 3866 - 3874 (2011)
(1R,2R,6S)-3-Methyl-6-(prop-1-en-2-yl)cyclohex-3-ene-1,2-diol 1 possesses potent antiparkinsonian activity in both MPTP and haloperidol animal models. The use of compound 1 resulted in nearly full recovery of the locomotor and exploratory activities and was as effective as the comparator agent (levodopa). All eight stereoisomers of compound 1 have been synthesized and the influence of the absolute configuration on the antiparkinsonian activity of compound 1 was shown.
Domino Mukaiyama-Michael reactions in the synthesis of polycyclic systems
Sarabèr, Florence C. E.,Dratch, Svetlana,Bosselaar, Geke,Jansen, Ben J. M.,De Groot, Aede
, p. 1717 - 1725 (2006)
Good results were obtained in the Mukaiyama-Michael reaction of the silyl enol ether of cyclohexanone with 2-methyl-2-cyclopentenone and carvone, with transfer of the silyl group to the receiving enone and with TrSbCl6 as catalyst. A second Mukaiyama-Michael reaction of this new silyl enol ether with methyl vinyl ketone and cyclization of the resulting adduct leads to tricyclic compounds in one-pot domino sequences. The scope and limitations of this domino reaction have been investigated.
Intramolecularly competitive Ireland-Claisen rearrangements: Scope and potential applications to natural product synthesis
Hong, Sang-Phyo,Lindsay, Harriet A.,Yaramasu, Tripura,Zhang, Xiaowei,McIntosh, Matthias C.
, p. 2042 - 2055 (2007/10/03)
A variety of bis-allylic esters were prepared by vinylmetal addition to cycloalkenones followed by esterification either in situ or in a separate operation. For chiral cyclohexenones, the vinyl additions generally occurred with > 10:1 diastereoselectivity. Although in some cases the bis-allylic esters proved to be sensitive to silica gel or other adsorbents, all of the esters examined could be isolated in acceptable purity. The Ireland-Claisen rearrangement of the bis-allylic esters occurred with complete regioselectivity via the exocyclic alkene. The alkene stereochemistry and the stereochemistry at C-2 and C-3 of the pentenoic acid products were consistent with a chairlike transition state in the rearrangement. Substituents at the carbons adjacent to the allylic carbinol carbon (i.e., C-2 or C-6 in cyclohexenone-derived substrates) directed the stereochemical course of the rearrangement. The rearrangements generally proceeded so as to place the larger of the C-2 or C-6 substituents in the pseudoequatorial position with respect to the chairlike transition state. For a bis-allylic ester bearing both a C-2-CH3 and a C-6-OMEM substituent, the rearrangement product resulted from the nominally smaller OMEM substituent occupying a pseudoequatorial position with respect to the chairlike transition state.
Synthesis of the A/B/C ring system of taxane diterpenes from (S)-(+)-carvone
Hirai, Yoshimasa,Ito, Kennosuke,Nagaoka, Hiroto
, p. 235 - 238 (2007/10/03)
A new route for the synthesis of the tricyclo[9.3.1.03,8]pentadecane skeleton, the A/B/C ring system of taxanes, via epoxide (12) from (5)-(+)-carvone using sequential Michael reaction followed by base-induced oxy-Cope rearrangement and Diels-A
