104410-87-9

Upstream product

• 109124-35-8 [(1S,2R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-formyl-propyl]-carbamic acid benzyl ester 
• 501-53-1 benzyl chloroformate 
• 104486-65-9 (4S,5S,6S)-6-[(1R,2R)-1-Benzyloxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-cyclohex-1-enecarboxylic acid methyl ester 
• 104410-81-3 (S)-6-[(1R,2R)-1-Benzyloxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-(tert-butyl-dimethyl-silanyloxy)-cyclohexa-1,4-dienecarboxylic acid methyl ester 
• 109215-73-8 >-<4-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-1-<1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>ethyl>-2,4-pentadienyl>carbamic acid phenylmethyl ester 
• 109215-72-7 >-<1-<1-<<(1,1-(dimethylethyl)dimethyl)silyl>oxy>ethyl>-4-oxo-2-pentenyl>carbamic acid phenylmethyl ester 
• 104410-78-8 (2S,3R)-methyl 2-(((benzyloxy)carbonyl)amino)-3-((tert-butyldimethylsilyl)oxy)butanoate 
• 19728-63-3 N-benzyloxycarbonyl-L-treonine 
• 57224-63-2 methyl (2S,3R)-2-(benzyloxycarbonylamino)-3-hydroxybutyrate 
• 104421-37-6 ((3R,4R,4aS,5S,6S)-5,6-Dihydroxy-3-methyl-1-oxo-3,4,4a,5,6,7-hexahydro-1H-isochromen-4-yl)-carbamic acid benzyl ester 
• 18162-48-6 tert-butyldimethylsilyl chloride 

Downstream Products

• 109124-38-1 ((3R,4R,4aS,5S,6S,8S,8aS)-5,6,8-Trihydroxy-3-methyl-1-oxo-octahydro-isochromen-4-yl)-carbamic acid benzyl ester 
• 104410-88-0 <3aS-(3aα,5α,6β,6aβ,7β,8β,10aS*)>-<5,6-bis<<(1,1-dimethylethyl)dimethylsilyl>oxy>hexahydro-8-methyl-10-oxo-2-thioxo-5H,10H-1,3-dioxolo<4,5-i><2>benzopyran-7-yl>carbamic acid phenylmethyl ester 
• 109124-37-0 [(3R,4R,4aS,5S,6S,8S,8aS)-5,6-Bis-(tert-butyl-dimethyl-silanyloxy)-8-hydroxy-3-methyl-1-oxo-octahydro-isochromen-4-yl]-carbamic acid benzyl ester 
• 109124-42-7 N-carbobenzoxy-5,6-O-isopropylidene-5,6,10-triepi-actinobolin 
• 109124-39-2 ((3aS,5S,5aS,8R,9R,9aS,9bS)-5-Hydroxy-2,2,8-trimethyl-6-oxo-octahydro-[1,3]dioxolo[4,5-f]isochromen-9-yl)-carbamic acid benzyl ester 
• 104410-89-1 <3aS-(3aα,8α,9α,9aα,9bβ)>-(3a,4,8,9,9a,9b-hexahydro-5-hydroxy-2,2,8-trimethyl-6-oxo-6H-1,3-dioxolo<4,5-f><2>benzopyran-9-yl)carbamic acid phenylmethyl ester 
• 104410-88-0 [(3aR,5S,6S,6aS,7R,8R,10aS)-5,6-Bis-(tert-butyl-dimethyl-silanyloxy)-8-methyl-10-oxo-2-thioxo-hexahydro-[1,3]dioxolo[4,5-i]isochromen-7-yl]-carbamic acid benzyl ester 
• 109124-36-9 [(3R,4R,4aS,5S,6S,8S,8aR)-5,6-Bis-(tert-butyl-dimethyl-silanyloxy)-8,8a-dihydroxy-3-methyl-1-oxo-octahydro-isochromen-4-yl]-carbamic acid benzyl ester 

Relevant academic research and scientific papers

π-Facial selection in intermolecular Diels-Alder reactions: Total syntheses of (+)-actinobolin and (+)-5,6,10-triepi-actinobolin

Syntheses of both 5,6,10-triepi-actinobolin and the antibiotic actinobolin are described in which a homochiral diene prepared from L-threonine is employed as a key componenet in a Diels-Alder reaction with an acetylenic dienophile. While the Diels-Alder reaction of this diene with methyl propiolate furnished the cycloadduct required for the synthesis of (+)-actinobolin as the minor diastereomer, the completion of the synthesis required but seven additional steps. The steric and stercoelectronic features responsible for the π-facial course of this cycloaddition reaction are discussed along with the various steps required to complete the syntheses of the title compounds.