176775-30-7

Upstream product

• 176656-16-9 tert-Butyl-[(4S,6R,9R)-2,2-dimethyl-4-((S)-1-methyl-allyl)-1,3,7-trioxa-spiro[5.5]undec-10-en-9-yloxy]-dimethyl-silane 
• 176656-15-8 (4S,6R,9R)-2,2-Dimethyl-4-((S)-1-methyl-allyl)-1,3,7-trioxa-spiro[5.5]undec-10-en-9-ol 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 176656-18-1 (E)-(R)-4-[(4S,6R,9R)-9-(tert-Butyl-dimethyl-silanyloxy)-2,2-dimethyl-1,3,7-trioxa-spiro[5.5]undec-10-en-4-yl]-1-[(1R,3R,4R)-4-(tert-butyl-diphenyl-silanyloxy)-3-methoxy-cyclohexyl]-2-methyl-pent-1-en-3-one 
• 143370-19-8 [(1R,2R,4R)-4-((E)-2-Bromo-propenyl)-2-methoxy-cyclohexyloxy]-tert-butyl-diphenyl-silane 
• 176656-14-7 (R)-2-[(4S,6R,9R)-9-(tert-Butyl-dimethyl-silanyloxy)-2,2-dimethyl-1,3,7-trioxa-spiro[5.5]undec-10-en-4-yl]-propionaldehyde 
• 143347-88-0 (R)-2,2-Dimethyl-4-((S)-1-methyl-allyl)-1,3,7-trioxa-spiro[5.5]undec-10-en-9-one 

Downstream Products

• 176775-32-9 (4S,6R,9R)-4-{(E)-(1R,2R)-2-(tert-Butyl-dimethyl-silanyloxy)-4-[(1R,3R,4R)-4-(tert-butyl-diphenyl-silanyloxy)-3-methoxy-cyclohexyl]-1,3-dimethyl-but-3-enyl}-2,2-dimethyl-1,3,7-trioxa-spiro[5.5]undec-10-en-9-ol 

Relevant academic research and scientific papers

A total synthesis of FK-506

A total synthesis of FK-506 (1) is presented. The synthesis features a highly convergent approach utilizing a block coupling strategy. Top and bottom half sections of the molecule are coupled by addition of a vinyl cuprate with a spiroenone. The α-allyl aldol functionality is revealed by a reductive opening of the spiroenone system. The labile α,β-diketoamide hemiketal portion of the molecule is prepared by a late stage generation and oxidation of a masked enediol. Top and bottom half segments are themselves derived by coupling of smaller subunits, resulting in a very convergent route.