104486-64-8

Upstream product

• 109215-73-8 >-<4-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-1-<1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>ethyl>-2,4-pentadienyl>carbamic acid phenylmethyl ester 
• 922-67-8 propynoic acid methyl ester 
• 57224-63-2 methyl (2S,3R)-2-(benzyloxycarbonylamino)-3-hydroxybutyrate 
• 19728-63-3 N-benzyloxycarbonyl-L-treonine 
• 104410-78-8 (2S,3R)-methyl 2-(((benzyloxy)carbonyl)amino)-3-((tert-butyldimethylsilyl)oxy)butanoate 
• 109215-72-7 >-<1-<1-<<(1,1-(dimethylethyl)dimethyl)silyl>oxy>ethyl>-4-oxo-2-pentenyl>carbamic acid phenylmethyl ester 
• 501-53-1 benzyl chloroformate 
• 109124-35-8 [(1S,2R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-formyl-propyl]-carbamic acid benzyl ester 

Downstream Products

• 104410-84-6 <3R-(3α,4α,4aβ,5β,6α)>-(3,4,4a,5,6,7-hexahydro-5,6-dihydroxy-3-methyl-1-oxo-1H-2-benzopyran-4-yl)carbamic acid phenylmethyl ester 
• 104427-25-0 (4R,5R,6R)-6-[(1R,2R)-1-Benzyloxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-cyclohex-1-enecarboxylic acid methyl ester 
• 104427-25-0 <4R-<4α,5β,6α(1R*,2R*)>>-4-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-6-<2-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-1-<<(phenylmethoxy)carbonyl>amino>propyl>-5-hydroxy-1-cyclohexene-1-carboxylic acid methyl ester 
• 109124-43-8 <1aR-(1aα,3α,4β,4aβ,5α,6α,6α,8aS*)>-(hexahydro-3,4-dihydroxy-6-methyl-8-oxo-3H,8H-oxireno<2>benzopyran-5-yl)carbamic acid phenylmethyl ester 
• 109124-45-0 C₂₄H₃₁NO₇ 
• 109124-46-1 <3'aR-(3'aα,8'β,9'β,9'aα,9'bβ)>-(3'a,4',8',9',9'a,9'b-hexahydro-5'-hydroxy-8'-methyl-6'-oxospirodioxolo<4,5f><2>benzopyran>-9'-yl)carbamic acid phenylmethyl ester 
• 109124-47-2 C₂₇H₃₄N₂O₈ 
• 109124-44-9 ((3R,4R,4aR,5R,6R,8R,8aS)-5,6,8-Trihydroxy-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.

A Total Synthesis of Actinobolin via the Intermolecular Diels-Alder Reaction of a Threonine-derived Diene

A sixteen-step synthetic route to (+)-actinobolin from L-threonine is described.