247577-92-0

Upstream product

• 176545-65-6 5-[(tert-butyldimethylsilyl)oxy]-1-(trimethylsilyl)pent-1-yn-3-ol 
• 89922-82-7 3-(tert-butyldimethylsilanyloxy)propionaldehyde 
• 73842-99-6 3-tert-butyldimethylsilyloxy-1-propanol 
• 479581-79-8 5-(tert-butyldimethylsiloxy)-3-(tert-butyldiphenylsiloxy)-1-pentyne 

Downstream Products

• 668475-60-3 3-[3-(tert-butyl-diphenyl-silanyloxy)-hept-6-en-4-ynyl]-3H-oxazol-2-one 
• 479581-90-3 3-[(3-tert-butyldiphenylsiloxy)-6-hydroxy-4-heptynyl]-2-oxazolone 
• 479581-89-0 3-[3-(tert-butyldiphenylsiloxy)-4-pentynyl]-2-oxazolone 
• 479581-88-9 3-(tert-butyldiphenylsiloxy)-5-iodo-1-pentyne 

Relevant academic research and scientific papers

Studies on the Total Synthesis of Streptazolin and Its Related Natural Products: First Total Synthesis of (±)-8α-Hydroxystreptazolone

The intramolecular Pauson-Khand reaction of 2-oxazolone derivatives with a suitable heptynyl appendage gave exclusively the corresponding 4-hydroxy-6-substituted-9-oxa-1-azatricyclo[6.2.1.0 5,11]-undec-5-ene-7,10-diones. On the basis of this newly developed Pauson-Khand reaction of 2-oxazolone-alkyne derivatives, the first total synthesis of (±)-8α-hydroxystreptazolone was accomplished in a highly stereoselective manner. In addition, (±)-7-epi-8α -hydroxystreptazolone was also synthesized.

Total synthesis of (+/-)-8alpha-hydroxystreptazolone.

[reaction: see text] The intramolecular Pauson-Khand reaction of 2-oxazolone derivatives with a suitable pentynyl appendage exclusively gave the corresponding 4-hydroxy-6-substituted-9-oxa-1-azatricyclo[6.2.1.0(5,11)]undec-5-en-7,10-diones. Based on this newly developed Pauson-Khand reaction of 2-oxazolone-alkyne derivatives, the first total synthesis of (+/-)-8alpha-hydroxystreptazolone was accomplished in a highly stereoselective manner.