118968-10-8

Upstream product

• 119066-22-7 (1S)-(1,3/2,4)-1,2,3-triacetoxy-4-benzoyloxymethylcyclohex-5-ene 
• 119066-23-8 (1R,3R,6R,9S,10S)-9,10-dihydroxy-3-phenyl-2,4-dioxabicyclo<4.4.0>dec-7-ene 
• 119067-99-1 (-)-(1R,2R,3R,4S)-1-(hydroxymethyl)cyclohex-5-ene-2,3,4-triol 
• 90025-03-9 (1S)-(1,3,6/2)-4-acetoxymethyl-1,2,3-tri-O-acetyl-6-azido-4-cyclohexene-1,2,3-triol 
• 114779-28-1 (1R,3R,6R,9S,10S)-9,10-dibenzyloxy-3-phenyl-2,4-dioxabicyclo<4.4.0>dec-7-ene 
• 97747-51-8 (1R)-(-)-1,2,3-tri-O-acetyl-(1,3/2,4,6)-4-bromo-6-bromomethyl-1,2,3-cyclohexanetriol 
• 100-39-0 benzyl bromide 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 114779-32-7 1D-(1,3,6/2)-6-amino-4-benzyloxymethyl-1,2,3-tri-O-benzyltrihydroxycyclohex-4-ene 
• 114779-35-0 (1R,2S,5R,7R,8R,9R,10R)-8,9-dibenzyloxy-5-phenyl-4,6,11-trioxatricyclo<8.1.0.0^2.7>undecane 
• 114779-35-0 (1aR,2S,3S,3aR,5R,7aS,7bR)-2,3-Bis-benzyloxy-5-phenyl-hexahydro-1,4,6-trioxa-cyclopropa[a]naphthalene 

Relevant academic research and scientific papers

Synthetic studies on antibiotic validamycins. Part 13. Total synthesis of (+)-validamycins A and E, and related compounds

(+)-Validoxylamine A (1) has been completely synthesized by deoxygenation of the validoxylamine B derivative (6) through formation of the aziridine, nucleophilic displacement with toluenethiol, reduction with Raney nickel, and deprotection. The validoxylamine A derivative (10) obtained was convertible, by glycosylation followed by deprotection, into validamycins A (2), E (3), and their analogues, which constitutes a total synthesis thereof.

SYNTHETIC STUDIES ON ANTIBIOTIC VALIDAMYCINS. PART 12. TOTAL SYNTHESIS OF (+)-VALIDAMYCIN B AND (+)-VALIDOXYLAMINE B

The first complete synthesis of validamycin B (1a) and validoxylamine B (2a) is reported; coupling of the epoxide (12) and the partially protected derivative (16) of (+)-valienamine, followed by deprotection, gives (1a), which was identified from the 1H n

Total Synthesis of (+)-Validoxylamine A

(+)-Validoxylamine A was synthesized by selective deoxygenation of (+)-validoxylamine B derivative, which was obtained by the coupling of the partially protected (+)-valienamine and (1R,2S,5R,7R,8R,9R,10R)-8,9-dibenzyloxy-5-phenyl-4,6,11-trioxatricyclo8.