174757-50-7

Upstream product

• 185335-97-1 Toluene-4-sulfonic acid (2R,3S,4R)-4-(tert-butyl-dimethyl-silanyloxy)-2,3-dihydroxy-4-phenyl-butyl ester 
• 174647-71-3 (1R,2S,3S)-1-(t-butyldiphenylsilyloxy)-1-phenyl-4-(p-toluenesulfonyloxy)butane-2,3-diol 

Downstream Products

• 96422-53-6 (6R,7R,8R)-goniodiol-7-monoacetate 
• 214678-55-4 (R)-4-Benzenesulfonyl-6-((1R,2R)-1,2-dihydroxy-2-phenyl-ethyl)-tetrahydro-pyran-2-one 
• 146236-73-9 (+)-goniodiol 
• 136778-40-0 7,8-di-O-acetyl-goniodiol 
• 144429-71-0 (6R,7R,8R)-goniodiol-8-monoacetate 
• 185216-23-3 (1R,2S,3R)-3,4-epoxy-1,2-isopropylidenedioxy-1-phenylbutane 

Relevant academic research and scientific papers

Easy access to an enantiopure precursor of (+)-goniodiol

Asymmetric synthesis of the epoxide 2 has been achieved from (R)-mandelic acid 3 via highly diastereoselective Wittig reaction and erythro-selective OsO4 catalyzed cis-hydroxylation as key steps. Copyright (C) Elsevier Science Ltd.

Total synthesis of (+)-goniodiol

Cytotoxic styryl lactone, (+)-goniodiol 1, was prepared in enantioenriched form (33 92%) in 15 steps from the α-(α'-alkoxyallenic) alcohol 5.

Enantioselective synthesis of (+)-goniodiol and of its naturally occurring acetylated analogs

A novel route to enantioenriched (+)-goniodiol and its natural acetylated derivatives, potent cytotoxic compounds, is described. The main features of this synthesis are transfer of the asymmetric information of the scalemic allenic alcohol 5 to the α- and β- carbons through highly diastercoselective reactions and introduction of the α,β-unsaturated lactone moiety by the Ghosez' methodology.