345896-87-9

Upstream product

• 345896-86-8 (2R,3S,5S,6S)-1-benzoyl-5{[tert-butyl(diphenyl)silyl]oxy}-2-[(3R)-3-hydroxy-5-(methoxymethoxy)pentyl]-6-methyl-3-piperidinol 
• 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 
• 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 
• 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 
• 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 
• 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 
• 303190-96-7 (3S,4E,6E)-4-(benzyloxy)-9-(methoxymethoxy)-4,6-nonadien-1-ol 
• 303190-95-6 (2S,4S)-4-[(1E,3E)-6-(methoxymethoxy)-1,3-hexadienyl]-2-phenyl-1,3-dioxane 
• 303190-94-5 (3E,5E)-6-[(2S,4S)-2-phenyl-1,3-dioxan-4-yl]-3,5-hexadien-1-ol 

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.