81418-10-2

Upstream product

• 86668-63-5 8-hydroxy-1-acetoxy-1(R*),4,4a(S*),9a(S*)-tetrahydroanthraquinone 
• 1194750-34-9 8,9-dihydroxy-1-acetoxy-10-oxo-1(R*),4,4a(S*),9(R*),9a(R*),10-hexahydroanthracene 
• 86668-41-9 1-acetoxy-10-(tert-butyldimethylsiloxy)-8,9-(di-tert-butylsilylenedioxy)-1(R*),4,4a(S*),9(R*),9a(S*),10(S*)-hexahydroanthracene 
• 86668-44-2 1-hydroxy-10-(tert-butyldimethylsiloxy)-8,9-(di-tert-butylsilylenedioxy)-1(R*),4,4a(S*),9(R*),9a(S*),10(S*)-hexahydroanthracene 
• 86668-46-4 10-(tert-butyldimethylsiloxy)-8,9-(di-tert-butylsilylenedioxy)-1-oxo-1,4,4a(S*),9(R*),9a(R*),10(S*)-hexahydroanthracene 
• 86668-39-5 10-hydroxy-1-acetoxy-8,9-(di-tert-butylsilylenedioxy)-1(R*),4,4a(S*),9(R*),9a(S*),10(S*)-hexahydroanthracene 
• 81418-04-4 1-acetoxy-8,9-(di-tert-butylsilylenedioxy)-10-oxo-1(R*),4,4a(S*),9(R*),9a(S*),10-hexahydroanthracene 
• 65174-11-0 1-acetoxy-2-(4'-methoxyphenylthio)-1-cyclobutene 
• 65174-13-2 2-acetoxy-3-(4'-methoxyphenylthio)-1,3-butadiene 
• 81418-09-9 2-acetoxy-6-(tert-butyldimethylsiloxy)-10,11-(di-tert-butylsilylenedioxy)-3-((4'-methoxyphenyl)thio)-12-oxo-1,4,4a(R*),5,5a(S*),6(S*),11(R*),11a(R*),12,12a(S*)-decahydronaphthacene 

Downstream Products

• 86668-47-5 10,12-dihydroxy-2-acetoxy-6-(tert-butyldimethylsiloxy)-3-((4'-methoxyphenyl)thio)-11-oxo-1,4,4a(R*),5,5a(S*),6(S*),11,12a(S*)-octahydronaphthacene 

Relevant academic research and scientific papers

Sulfur-Substituted Dienes and the Silylene Protecting Group in Synthesis. Deoxypillaromycinone

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.