303191-07-3

Upstream product

• 75-15-0 carbon disulfide 
• 303191-06-2 (3S)-1-((2R,3S,5S,6S)-1-benzoyl-3-(benzyloxy)-5-{[tert-butyl(diphenyl)silyl]oxy}-6-methyl-piperidinyl)-5-(methoxymethoxy)-3-pentanol 
• 74-88-4 methyl iodide 
• 345896-85-7 (S)-1-[(2R,3S,5S,6S)-3-Benzyloxy-5-(tert-butyl-diphenyl-silanyloxy)-6-methyl-piperidin-2-yl]-5-methoxymethoxy-pentan-3-ol 
• 164471-44-7 ethyl E-3-<(2S,4S)-2-phenyl-1,3-dioxan-4-yl>prop-2-en-ol 
• 164577-87-1 ethyl E-3-<(2S,4S)-2-phenyl-1,3-dioxan-4-yl>prop-2-enoate 
• 303191-04-0 (2S,4aR,5S,7S)-5-(benzyloxy)-7-{[tert-butyl(diphenyl)silyl]oxy}-2-[2-(methoxymethoxy)ethyl]hexahydropyrido[1,2-b][1,2]oxazin-8(2H)-one 
• 303191-05-1 (2S,4aR,5S,7S,8R)-5-(benzyloxy)-7-{[tert-butyl(diphenyl)silyl]oxy}-2-[2-(methoxymethoxy)ethyl]-8-methyloctahydropyrido[1,2-b][1,2]oxazin 
• 345896-76-6 (3S,4E,6E)-4-(benzyloxy)-9-(methoxymethoxy)-4,6-nonadienyl 4-methylbenzenesulfonate 
• 303191-02-8 (2S,4aR,5S)-5-(benzyloxy)-2-[2-(methoxymethoxy)ethyl]hexahydropyrido[1,2-b][1,2]-oxazin-8(2H)-one 
• 303190-98-9 (4S,5E,7E)-4-(benzyloxy)-N-hydroxy-10-(methoxymethoxy)-5,7-decadienamide 
• 303190-97-8 methyl (4S,5E,7E)-4-(benzyloxy)-10-(methoxymethoxy)-5,7-decadienoate 
• 303191-00-6 (2R,4aR,5S)-5-(benzyloxy)-2-[-(methoxymethoxy)ethyl]-4a,5,6,7-tetrahydropyrido[1,2-b][1,2]oxazin-8(2H)-one 
• 345896-77-7 (4S,5E,7E)-4-(benzyloxy)-10-(methoxymethoxy)-5,7-decadienenitrile 

Downstream Products

• 303191-13-1 methyl (2S,3S,5S,8aR)-1-benzoyl-3-hydroxy-2-methyl-1,2,3,5,6,7,8,8a-octahydro-5-quinolinecarboxylate 
• 303191-12-0 methyl (2S,3S,5R,8aR)-1-benzoyl-3-hydroxy-2-methyl-1,2,3,5,6,7,8,8a-octahydro-5-quinolinecarboxylate 
• 303191-14-2 ((2S,3S,5R,8aR)-1-benzyl-3-{[tert-butyl(dimethyl)silyl]oxy}-2-methyl-1,2,3,5,6,7,8,8a-octahydro-5-quinolinyl)methanol 
• 345897-03-2 methyl (2S,3S,5R,8aR)-1-benzoyl-3-{[tert-butyl(dimethyl)silyl]oxy}-2-methyl-1,2,3,5,6,7,8,8a-octahydro-5-quinolinecarboxylate 
• 303191-08-4 5-((2R,5S,6S)-1-benzoyl-5-{[tert-butyl(diphenyl)silyl]oxy}-6-methyl-3-oxopiperidinyl)pentanal 
• 303191-11-9 methyl (2S,3S,5S,8aR)-1-benzoyl-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methyl-1,2,3,5,6,7,8,8a-octahydro-5-quinolinecarboxylate 
• 303191-09-5 (2S,3S,4aR,5S,8aR)-1-benzoyl-3-{[tert-butyl(diphenyl)silyl]oxy}-4a-hydroxy-2-methyldecahydro-5-quinolinecarbaldehyde 
• 345896-93-7 (2R,3S,5S,6S)-1-benzoyl-5-{[tert-butyl(diphenyl)silyl]oxy}-2-(5-hydroxypentyl)-6-methyl-3-piperidinol 
• 303191-10-8 methyl (2S,3S,4aR,5S,8aR)-1-benzoyl-3-{[tert-butyl(diphenyl)silyl]oxy}-4a-hydroxy-2-methyldecahydro-5-quinolinecarboxylate 
• 345896-91-5 5-((2R,3S,5S,6S)-1-benzoyl-3-(benzyloxy)-5-{[tert-butyl(diphenyl)silyl]oxy}-6-methyl-3-piperidinyl)-1-pentanol 
• 345896-89-1 (2R,3S,5S,6S)-1-benzoyl-3-(benzyloxy)-5-{[tert-butyl(diphenyl)silyl]oxy}-2-[5-(methoxymethoxy)pentyl]-6-methylpiperidine 

Relevant academic research and scientific papers

Total synthesis of the marine alkaloids (-)-lepadins A, B, and C based on stereocontrolled intramolecular acylnitroso-diels-alder reaction

The first syntheses of (-)-lepadins A and C, as well as a new synthesis of (-)-lepadin B, have been achieved from commercially available (S)-malic acid. The methodology is based on an intramolecular hetero-Diels-Alder reaction of the acylnitroso compound, affording the bicyclic oxazino lactam with trans selectivity, which was converted to the cis-decahydroquinoline via asymmetric enolate hydroxylation followed by intramolecular aldol cyclization. The total syntheses proceed by employing cis-decahydroquinoline bearing the (E)-iodoalkenyl group as the common key intermediate, which underwent a convergent coupling with the (E)-hexenyl unit via a palladium-catalyzed Suzuki cross-coupling reaction for the elaboration of the octadienyl side chain at the C5 position.