158010-33-4

Upstream product

• 112-29-8 1-bromo dodecane 
• 862603-26-7 (2S,5R,2'S,5'R)-5'-Benzyloxymethyl-octahydro-[2,2']bifuranyl-5-carbaldehyde 
• 100-39-0 benzyl bromide 
• 81096-93-7 (R)-1-O-benzyl-1,2,4-butanetriol 
• 158010-22-1 (2S,5S,2S',5R')-5-<5'-<(Benzyloxy)methyl>tetrahydrofuran-2'-yl>-1,2-O-isopropylidenepentane-1,2,5-triol 
• 158010-24-3 (2R,5S,2'S,5'R)-5-<5'-<(Benzyloxy)methyl>tetrahydrofuran-2'-yl>tetrahydrofuran-2-methanol 
• 158110-03-3 (2S,5R)-5-<(Benzyloxy)methyl>tetrahydrofuran-2-methanol 
• 862603-76-7 1-((2S,5R,2'S,5'R)-5'-Benzyloxymethyl-octahydro-[2,2']bifuranyl-5-yl)-undecan-1-ol 
• 170305-54-1 (2S,5R)-5-<(Benzyloxy)methyl>tetrahydrofuran-2-carboxaldehyde 
• 115369-24-9 Toluene-4-sulfonic acid (R)-4-benzyloxy-3-hydroxy-butyl ester 
• 862603-74-5 Toluene-4-sulfonic acid (S)-3-((2S,5R)-5-benzyloxymethyl-tetrahydro-furan-2-yl)-3-[(E)-2-((S)-toluene-4-sulfinyl)-vinyloxy]-propyl ester 
• 862603-13-2 Toluene-4-sulfonic acid (R)-4-benzyloxy-3-[(E)-2-((R)-toluene-4-sulfinyl)-vinyloxy]-butyl ester 
• 862603-22-3 (2R,5S)-2-Benzyloxymethyl-5-{(S)-3-iodo-1-[(E)-2-((S)-toluene-4-sulfinyl)-vinyloxy]-propyl}-tetrahydro-furan 
• 862603-24-5 (2S,5R,2'S,5'R)-5'-Benzyloxymethyl-5-((S)-toluene-4-sulfinylmethyl)-octahydro-[2,2']bifuranyl 

Downstream Products

• 862603-47-2 (S)-3-((E)-(R)-13-{(2S,5R,2'S,5'R)-5'-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-undecyl]-octahydro-[2,2']bifuranyl-5-yl}-13-hydroxy-tridec-10-enyl)-5-methyl-3-phenylsulfanyl-dihydro-furan-2-one 
• 862604-08-8 (S)-3-((R)-13-{(2S,5R,2'S,5'R)-5'-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-undecyl]-octahydro-[2,2']bifuranyl-5-yl}-13-hydroxy-tridecyl)-5-methyl-3-phenylsulfanyl-dihydro-furan-2-one 
• 862603-35-8 (S)-3-((E)-(2R,11R)-2-(tert-Butyl-dimethyl-silanyloxy)-11-{(2S,5R,2'S,5'R)-5'-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-undecyl]-octahydro-[2,2']bifuranyl-5-yl}-11-hydroxy-undec-8-enyl)-5-methyl-3-phenylsulfanyl-dihydro-furan-2-one 
• 862604-04-4 (S)-3-((2R,11R)-2-(tert-Butyl-dimethyl-silanyloxy)-11-{(2S,5R,2'S,5'R)-5'-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-undecyl]-octahydro-[2,2']bifuranyl-5-yl}-11-hydroxy-undecyl)-5-methyl-3-phenylsulfanyl-dihydro-furan-2-one 
• 862603-31-4 (S)-3-((E)-(2R,13R)-2-(tert-Butyl-dimethyl-silanyloxy)-13-{(2S,5R,2'S,5'R)-5'-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-undecyl]-octahydro-[2,2']bifuranyl-5-yl}-13-hydroxy-tridec-10-enyl)-5-methyl-3-phenylsulfanyl-dihydro-furan-2-one 
• 862603-95-0 (S)-3-((2R,13R)-2-(tert-Butyl-dimethyl-silanyloxy)-13-{(2S,5R,2'S,5'R)-5'-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-undecyl]-octahydro-[2,2']bifuranyl-5-yl}-13-hydroxy-tridecyl)-5-methyl-3-phenylsulfanyl-dihydro-furan-2-one 
• 1028286-14-7 (2S,5R,2'S,5'R)-5'-[(S)-1-(tert-Butyl-diphenyl-silanyloxy)-undecyl]-octahydro-[2,2']bifuranyl-5-carbaldehyde 
• 158010-26-5 {(2S,5R,2'S,5'R)-5'-[(S)-1-(tert-Butyl-diphenyl-silanyloxy)-undecyl]-octahydro-[2,2']bifuranyl-5-yl}-methanol 

Relevant academic research and scientific papers

Stereoselective syntheses of rolliniastatin 1, rollimembrin, and membranacin

A radical cyclization of β-alkoxyvinyl sulfoxides-Pummerer rearrangement-allylation protocol was successfully applied to the synthesis of the threol cis/threol cis/erythro bis-oxolane moiety in rolliniastatin 1 (1), rollimembrin (2), and membranacin (3).

Total synthesis of (+)-rolliniastatin 1

The first total synthesis of the naturally occurring acetogenin (+)-rolliniastatin 1 (1) has been achieved. A high degree of stereochemical control in the construction of the bis-THF system was accomplished by chelation controlled addition of functionalized organo-metallic reagents derived from 5 and 11 to α-alkoxy-aldehydes.