1027259-59-1

Upstream product

• 76513-69-4 (2-trimethylethylsilylethoxy)methyl chloride 
• 482351-22-4 (5R,6R)-5-[(1E)-3-[(4-methoxyphenyl)methoxy]-1-[[[tris-(1-methylethyl)silyl]oxy]methyl]-1-propenyl]-2-(2-nitrophenyl)-6-[[[2-(trimethylsilyl)ethoxy]methoxy]methyl]-2-cyclohexen-1-one 
• 482351-12-2 (5R,6R)-6-hydroxymethyl-5-[(1E)-3-[(4-methoxyphenyl)methoxy]-1-[[[tris-(1-methylethyl)silyl]oxy]methyl]-1-propenyl]-2-cyclohexen-1-one 
• 482351-10-0 (3R)-3-[(1E)-3-[(4-methoxyphenyl)methoxy]-1-[[[tris-(1-methylethyl)silyl]oxy]methyl]-1-propenyl]cyclohexanone 
• 76074-18-5 trimethyl-(2-nitro-phenyl)-stannane 
• 122807-21-0 2,2-bis(ethylthio)ethylamine 
• 482351-14-4 (5R,6R)-6-hydroxymethyl-5-[(1E)-3-[(4-methoxyphenyl)methoxy]-1-[[[tris-(1-methylethyl)silyl]oxy]methyl]-1-propenyl]-2-(2-nitrophenyl)-2-cyclohexen-1-one 
• 482351-07-5 (5R,6R)-5-[(1E)-1-(hydroxymethyl)-3-[(4-methoxyphenyl)methoxy]-1-propenyl]-2-(2-nitrophenyl)-6-[[[2-(trimethylsilyl)ethoxy]methoxy]methyl]-2-cyclohexen-1-one 
• 482351-13-3 (5R,6R)-6-hydroxymethyl-2-iodo-5-[(1E)-3-[(4-methoxyphenyl)methoxy]-1-[[[tris-(1-methylethyl)silyl]oxy]methyl]-1-propenyl]-2-cyclohexen-1-one 

Downstream Products

• 509-40-0 diaboline 
• 482351-15-5 (6R,16α,19E)-1,2,19,20-tetradehydro-6-(ethylthio)-18-[(4-methoxyphenyl)methoxy]-17-[[2-(trimethylsilyl)ethoxy]methoxy]curan 
• 482351-05-3 (6R,16α,19E)-19,20-didehydro-6-(ethylthio)-18-[(4-methoxyphenyl)methoxy]-17-[[2-(trimethylsilyl)ethoxy]methoxy]curan 
• 793724-08-0 C₂₉H₃₆N₂O₃S(C₂H₂O) 
• 482351-31-5 C₃₅H₅₀N₂O₄SSi 
• 482351-06-4 (1S,4E,5R,6R)-2-[2,2-bis(ethylthio)ethyl]-2,3,4,5,6,7-hexahydro-4-[2-[(4-methoxyphenyl)methoxy]ethylidene]-6-[[[2-(trimethylsilyl)ethoxy]methoxy]methyl]-1,5-methano-1H-azocino[4,3-b]indole 

Relevant academic research and scientific papers

Enantioselective total synthesis of (-)-strychnine: Development of a highly practical catalytic asymmetric carbon-carbon bond formation and domino cyclization

An enantioselective total synthesis of (-)-strychnine was accomplished through the use of the highly practical catalytic asymmetric Michael reaction (0.1 mol% of (R)-ALB, greater than kilogram scale, without chromatography, 91% yield and >99% ee), and a domino cyclization that simultaneously constructed the B- and D- rings of strychnine (>77% yield). Newly-developed reaction conditions for thionium ion cyclization, NaBH3CN reduction of the imine moiety in the presence of a Lewis acid to prevent the ring-opening reaction, and chemoselective reduction of the thioether (desulfurization) in the presence of exocyclic olefin were pivotal to complete the synthesis. The described chemistry paves the way for the synthesis of more advanced Strychnos alkaloids. Graphical Abstract.

Enantioselective total synthesis of (-)-strychnine using the catalytic asymmetric Michael reaction and tandem cyclization

The enantioselective total synthesis of (-)-strychnine was accomplished through the use of the highly practical catalytic asymmetric Michael reaction (0.1 mol % of (R)-ALB, more than kilogram scale, without chromatography, 91% yield and >99% ee) as well as a tandem cyclization that simultaneously constructed B- and D-rings (>77% yield). Moreover, newly developed reaction conditions for thionium ion cyclization, NaBH3CN reduction of the imine moiety in the presence of Lewis acid to prevent ring opening reaction, and chemoselective reduction of the thioether (desulfurization) in the presence of exocyclic olefin were pivotal to complete the synthesis. The described chemistry paves the way for the synthesis of more advanced Strychnos alkaloids. Copyright