155530-52-2

Upstream product

• 155530-49-7 benzyl benzyl(3-oxopropyl)carbamate 
• 13504-77-3 methyl 2-bromo-2-(triphenylphosphanylidene)acetate 
• 123934-05-4 benzyl N-benzyl-N-(3-butenyl)carbamate 

Downstream Products

• 155530-59-9 5-(N-benzyl-N-benzyloxycarbonylamino)-2-vinylpent-2(E)-enoic acid methyl ester 
• 449143-38-8 4-[N-benzyl-N-4'-methoxycarbonylhexa-3'(Z),5'-dien-1'-yl]carbamoyl-2,3-dihydropyrrole-1-carboxylic acid ethyl ester 
• 155530-55-5 1-tert-butyl 8-methyl (2R,3aS,7aR,10aS)-5-benzyl-2-[(tert-butyldiphenylsilanyloxy)methyl]-4-oxo-2,3,5,6,7,7a,10,10a-octahydropyrrolo[2.3-i]isoquinoline-1,8(4H)-dicarboxylate 
• 155530-56-6 methyl (2R,3aS,7aR,10aS)-5-benzyl-2-[(tert-butyldiphenylsilanyloxy)methyl]-1-(hex-5-enoyl)-4-oxo-1,2,3,4,5,6,7,7a,10,10a-decahydropyrrolo[2.3-i]isoquinoline-8-carboxylate 
• 155530-54-4 2(R)-4-{N-benzyl-N-[4'-methoxycarbonylhexa-3'(E),5'-dien-1'-yl]carbamoyl}-2-(tert-butyldiphenylsilanyloxymethyl)-2,3-dihydropyrrole-1-carboxylic acid tert-butyl ester 
• 155530-60-2 methyl (2R,3aS,7aR,10aS)-5-benzyl-2-[(tert-butyl-diphenylsilanyloxy)methyl]-4-oxo-1,2,3,4,5,6,7,7a,10,10a-decahydropyrrolo[2.3-i]isoquinoline-8-carboxylate 
• 155530-62-4 (4aR,7aS,9R,10aS)-2-Benzyl-9-formyl-8-hex-5-enoyl-1-oxo-1,2,3,4,4a,7,7a,8,9,10-decahydro-pyrrolo[2,3-i]isoquinoline-5-carboxylic acid methyl ester 
• 155530-61-3 methyl (2R,3aS,7aR,10aS)-5-benzyl-2-hydroxymethyl-1-(hex-5-enoyl)-4-oxo1,2,3,4,5,6,7,7a,10,10a-decahydropyrrolo[2.3-i]isoquinoline-8-carboxylate 
• 155530-57-7 methyl (2R,3aS,7aR,10aS)-5-benzyl-1-(hex-5-enoyl)-4-oxo-2-vinyl-1,2,3,4,5,6,7,7a,10,10a-decahydropyrrolo[2.3-i]isoquinoline-8-carboxylate 
• 155530-53-3 5-(N-benzylamino)-2-vinylpent-2(E)-enoic acid methyl ester 
• 449143-39-9 1-ethyl 8-methyl (3aS,7aR,10aS)-5-benzyl-4-oxo-2,3,5,6,7,7a,10,10a-octahydropyrrolo[2.3-i]isoquinoline-1,8(4H)-dicarboxylate 

Relevant academic research and scientific papers

A NOVEL APPROACH TO THE ASYMMETRIC SYNTHESIS OF MANZAMINE A. CONSTRUCTION OF THE TETRACYCLIC ABCE RING SYSTEM

The enantiomerically pure tetracyclic ABCE subunit of manzamine A has been constructed by an intramolecular Diels-Alder reaction of the vinylogous imide 13 to give the ABC tricyclic core 14; elaboration of 14 into 16 followed by a novel olefin metathesis reaction to form the azocine ring then delivered the tetracycle 17.

Enantioselective total syntheses of manzamine A and related alkaloids

As a prelude to undertaking the total syntheses of the complex manzamine alkaloids, a series of model studies were conducted to establish the scope and limitations of intramolecular [4 + 2] cycloadditions of N-acylated vinylogous ureas with the trienic substrates 17a,b, 28a,b, and 34. These experiments clearly demonstrated that the geometry of the internal double bond and the presence of an electron-withdrawing group on the diene moiety were essential for the facile and stereoselective formation of the desired cycloadducts. The enantioselective syntheses of the manzamine alkaloids ircinol A (75), ircinal A (5), and manzamine A (1) were then completed by employing a convergent strategy that featured a novel domino Stille/Diels-Alder reaction to construct the tricyclic ABC ring core embodied in these alkaloids. Thus, the readily accessible chiral dihydropyrrole 58 was first converted in a single chemical operation into the key tricyclic intermediate 60. Two ring-closing metathesis reactions were then used to form the 13- and 8-membered rings leading to Z-72 and 74, the latter of which was quickly elaborated into ircinal A (5) via ircinol A (75). The synthetic 5 thus obtained was converted into manzamine A (1) following literature precedent. This concise synthesis of ircinal A required a total of 24 operations from commercially available starting materials with the longest linear sequence being 21 steps.