1429058-76-3

Upstream product

• 66416-72-6 4-bromo-2-iodoaniline 
• 1663-39-4 tert-Butyl acrylate 
• 556-56-9 allyl iodid 
• 1161719-82-9 (E)-tert-butyl 3-(2-amino-5-bromophenyl)acrylate 

Downstream Products

• 1429058-82-1 (3aR,9bS,αR)-N(1)-(α-methyl-4'-methoxybenzyl)-4-hydroxy-N(5)-(tert-butoxycarbonyl)-8-bromo-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2-c]quinolin-2-one 
• 1429058-84-3 (3aS,4S,9bS,αR)-N(1)-(α-methyl-4''-methoxybenzyl)-4-(2'-methoxy-2'-oxoethyl)-N(5)-(tert-butoxycarbonyl)-8-bromo-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2-c]quinolin-2-one 
• 1429058-85-4 (3aS,4S,9bS,αR)-N(1)-(α-methyl-4''-methoxybenzyl)-4-(2'-methoxy-2'-oxoethyl)-8-bromo-2,3,3a,4,5,9bhexahydro-1H-pyrrolo[3,2-c]quinolin-2-one 
• 1429058-78-5 tert-butyl (2R,3S,αR)-2-(2'-methoxy-2'-oxoethyl)-3-[N-allyl-N-(α-methyl-4'''-methoxybenzyl)amino]-3-(2''-N,N-diallylamino-5''-bromophenyl)propanoate 
• 1429058-79-6 C₂₅H₃₃BrN₂O₅ 
• 1429058-80-9 C₂₀H₁₉BrN₂O₃ 
• 1429058-81-0 (3aR,9bS,αR)-N(1)-(4'-methoxy-α-methylbenzyl)-5-(tert-butoxycarbonyl)-8-bromo-2,3,3a,4,5,9bhexahydro-1H-pyrrolo[3,2-c]quinolin-2,4-dione 
• 1429058-77-4 tert-butyl (3S,αR)-3-[N-allyl-N-(α-methyl-4''-methoxybenzyl)amino]-3-(2'-N,N-diallylamino-5'-bromophenyl)propanoate 

Relevant academic research and scientific papers

Asymmetric synthesis of (-)-martinellic acid

A high-yielding total asymmetric synthesis of (-)-martinellic acid is reported. The conjugate addition of lithium (R)-N-allyl-N-(α-methyl-4- methoxybenzyl)amide to tert-butyl (E)-3-[2′-(N,N-diallylamino)-5′- bromophenyl]propenoate and alkylation of the resultant β-amino ester have been used as the key steps to install the C(9b) and C(3a) stereogenic centers, respectively, and a highly diastereoselective Wittig reaction/intramolecular Michael addition was then used to create the C(4) stereogenic center within this tricyclic molecular architecture.

A diastereodivergent strategy for the asymmetric syntheses of (-)-martinellic acid and (-)-4-epi-martinellic acid

Asymmetric syntheses of (-)-martinellic acid and (-)-4-epi-martinellic acid were achieved in 20 steps from commercially available starting materials using a diastereodivergent strategy. The conjugate addition of lithium (R)-N-allyl-N-(α-methyl-p-methoxybenzyl)amide to tert-butyl (E)-3-[2′-(N,N-diallylamino)-5′-bromophenyl]propenoate and alkylation of the resultant β-amino ester with methyl bromoacetate were used as the key steps to install the C(9b) and C(3a) stereogenic centres, respectively. Subsequent cyclisation to the corresponding pyrroloquinolin-2-one and reduction of the C(4)-carbonyl group was followed by two complementary procedures for olefination and concomitant intramolecular Michael addition, which gave both C(4)-epimers of this tricyclic molecular architecture in >99:1 dr. Subsequent elaboration of these templates provided access to (-)-martinellic acid and, for the first time, (-)-4-epi-martinellic acid.