150831-56-4

Upstream product

• 3926-62-3 sodium monochloroacetic acid 
• 94790-24-6 (S)-methyl 2-((tert-butoxycarbonyl)amino)-3-(4-methoxyphenyl)propanoate 
• 4326-36-7 (S)-N-(tert-butoxycarbonyl)tyrosine methyl ester 

Downstream Products

• 1240017-61-1 C₁₆H₂₄ClNO₄ 
• 248948-75-6 (2S,5S,6S,7R,8S,10aS)-2-[[(benzyloxy)carbonyl]methylamino]octahydro-6-hydroxy-5-[(4-methoxyphenyl)methyl]-1H-7,10a-methanopyrrolo[1,2-a]azocin-8-yl dibenzyl phosphate 
• 333999-62-5 (1S,3S,6S,7S,8S,9S)-3-(N-benzyloxycarbonyl-N-methylamino)-6-(4-methoxybenzyl)-5-azatricyclo[6.3.1.0^1,5]dodecane-7,9-diol 
• 1449125-52-3 (2Z,5S,6S,7S,10aS)-6,8-bis{[tert-butyl(dimethyl)silyl]oxy}-2-(hydroxyimino)-5-(4-methoxybenzyl)-octahydro-3H-7,10a-methanopyrrolo[1,2-a]azocin-3-one 
• 1449125-48-7 (5S,6S,7S,10aR)-6,8-bis{[tert-butyl(dimethyl)silyl]oxy}-5-(4-methoxybenzyl)octahydro-3H-7,10amethanopyrrolo[1,2-a]azocin-3-one 
• 1449125-47-6 (5S,6S,7R,10aR)-8-{[tert-butyl(dimethyl)silyl]oxy}-6-hydroxy-5-(4-methoxybenzyl)octahydro-3H-7,10a-methanopyrrolo[1,2-a]azocin-3-one 
• 1240017-54-2 (5S,7S,10aR)-8-{[tert-butyl(dimethyl)silyl]oxy}-5-(4-methoxybenzyl)tetrahydro-1H-7,10a-methanopyrrolo[1,2-a]azocine-3,6(2H,5H)-dione 
• 1240017-60-0 (5S,6R,7R,10aR)-8-{[tert-butyl(dimethyl)silyl]oxy}-6-hydroxy-5-(4-methoxybenzyl)octahydro-3H-7,10a-methanopyrrolo[1,2-a]azocin-3-one 
• 1240017-59-7 (5S,6R,7S,10aR)-6,8-dihydroxy-5-(4-methoxybenzyl)octahydro-3H-7,10a-methanopyrrolo[1,2-a]-azocin-3-one 
• 1240017-65-5 (5S,6R,7R,10aR)-6-hydroxy-5-(4-methoxybenzyl)tetrahydro-1H-7,10a-methanopyrrolo[1,2-a]azocine-3,8(2H,5H)-dione 
• 1240017-64-4 (2S)-2-(2,8-dioxo-1-azaspiro[4.5]dec-1-yl)-3-(4-methoxyphenyl)propanal 
• 1240017-58-6 1-[(2S)-1-(4-methoxyphenyl)but-3-en-2-yl]-1-azaspiro[4.5]decane-2,8-dione 
• 1240017-56-4 8-{acetyl[(2S)-1-(4-methoxyphenyl)but-3-en-2-yl]amino}-N-(4-methoxyphenyl)-1,4-dioxaspiro[4.5]decane-8-carboxamide 
• 1163716-52-6 (2S)-1-(4-methoxyphenyl)but-3-en-2-amine 

Relevant academic research and scientific papers

Synthesis of the optically active key intermediate of FR901483

Efficient synthesis of the tricyclic key intermediate 2 for (-)-FR901483 1 was accomplished. The precursor of the intramolecular aldol reaction 4b is constructed by the Ugi 4CC reaction and subsequent intramolecular Dieckmann condensation. This approach allows a fully stereocontrolled total synthesis of (-)-FR901483, which would provide various derivatives.

Stereocontrolled total synthesis of (-)-FR901483

The total synthesis of a potent immunosuppressant (-)-FR901483 is accomplished. The skeleton itself is constructed by the Ugi 4CC reaction, subsequent intramolecular Dieckmann condensation, and a diastereoselective intramolecular aldol reaction. However, the remarkable feature is the stereoselective incorporation of the p-methoxybenzyl and methylamino groups within the tricyclic core skeleton.