427897-82-3

Upstream product

• 427897-79-8 (1S,2S,5S)-2-[3-(tert-butyldimethylsilanyloxy)propyl]-4-(tert-butyldiphenylsilanyloxymethyl)-1-hydroxy-2,5-dimethyl-3-cyclohexene-1-carboxaldehyde 
• 427897-76-5 [(1S,2S,5S)-2-[3-(tert-butyldimethylsilanyloxy)propyl]-4-(tert-butyldiphenylsilanyloxymethyl)-2,5-dimethylcyclohex-3-enyl]-(10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-azatricyclo[5.2.1.0^1,5]dec-4-yl)-methanone 
• 427897-77-6 (1S,2S,5S)-2-[3-(tert-butyldimethylsilanyloxy)propyl]-4-(tert-butyldiphenylsilanyloxymethyl)-2,5-dimethyl-3-cyclohexene-1-carboxaldehyde 
• 193292-38-5 (2Z,4E)-8-[(tert-butyldimethylsilyl)oxy]-3-[[(tert-butyldiphenylsilyl)oxy]methyl]-5-methyl-2,4-octadiene 
• 108-24-7 acetic anhydride 
• 427897-81-2 (1S,2S,5S)-4-(tert-butyldiphenylsilanyloxymethyl)-1-hydroxy-2-(3-hydroxypropyl)-2,5-dimethyl-3-cyclohexene-1-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Diastereoselective synthesis of the endo- and exo-spirotetronate subunits of the quartromicins. The first enantioselective Diels-Alder reaction of an acyclic (Z)-1,3-diene.

[reaction: see text]. Diastereoselective syntheses of the endo- and exo-spirotetronates 1 and 2, corresponding to the galacto and agalacto fragments of quartromicins A3 and D3, are described. The key step of these syntheses are highly enantio- and diastereoselective Lewis acid catalyzed Diels-Alder reactions of the 1,1,3,4-tetrasubstituted diene 3.

Studies on the synthesis of the quartromicins: Partial stereochemical assignment of quartromicins A3 and D3 and diastereoselective synthesis of the endo- and exo-spirotetronate subunits

A partial stereochemical assignment of quartromicins A3 and D3 is presented, along with diastereoselective syntheses of the endo- and exo-spirotetronates 1 and 2, corresponding to the galacto and agalacto fragments of the proposed quartromicin stereostructure. The key steps of these syntheses are highly enantio- and diastereoselective Lewis acid catalyzed Diels-Alder reactions of 1,1,3,4-tetrasubstituted diene 24.