86668-63-5Relevant articles and documents
The 'Mikami'-catalyst in enantioselective diels-alder reactions of juglone-based dienophiles with different 1-oxygenated dienes: An investigation on the substitution pattern dependent regioselectivity
B?se, Dietrich,Frey, Wolfgang,Pietruszka, J?rg
, p. 2524 - 2532 (2014/11/08)
A mechanistic study investigating the substitution pattern depending regioselectivity of enantioselective BINOL-Ti-catalyzed Diels-Alder reactions of juglone-based dienophiles with 1-oxygenated dienes is reported. The different influences of residues both on the diene as well as on the dienophiles are investigated giving a detailed picture of their role on the regioselectivity.
Sulfur-Substituted Dienes and the Silylene Protecting Group in Synthesis. Deoxypillaromycinone
Trost, Barry M.,Caldwell, Charles G.,Murayama, Eigoro,Heissler, Denis
, p. 3252 - 3265 (2007/10/02)
A general approach directed toward the anthracycline antitumor compounds and the tetracycline antibiotics evolves from the sequential use of a 1-oxy- and 2-oxybuta-1,3-diene in regiocontrolled Diels-Alder reactions with juglone.By appropriately choosing the 1-(acyloxy)buta-1,3-diene, the absolute as well as relative stereochemistry of the final products is controlled. 2-Acetoxy-3-p-anisylthiobuta-1,3-diene controlls the orientation of the second cycloaddition and permits direct introduction of the enone functionality.The success of this second Diels-Alder reaction with a very sensitive cyclohexenone as a dienophile attests to its extraordinary reactivity and therefore utility in synthesis.The elaboration of the A ring functionality of pillaromycinone employs a cis hydroxylation and conversion of the cyclohexanone unit to a 1-acetylcyclohexene system via singlet oxygen oxidation of a homologated enol ether.Aromatization then completes the synthesis of deoxypillaromycinone.The virtues of the di-tert-butylsilyl protecting group for 1,2- and 1,3-diols are summarized.