165258-13-9

Upstream product

• 165258-08-2 Methyl 5-(benzyloxy)-8-bromo-1,4,7-trimethoxy-6-methylnaphth-3-oate 
• 165258-07-1 Methyl 5-(benzyloxy)-1,4,7-trimethoxy-6-methylnaphth-3-oate 
• 165258-06-0 5-(Benzyloxy)-1,4,7-trimethoxy-6-methyl-3-naphthoic acid 
• 165258-05-9 5-(Benzyloxy)-3-bromo-1,4,7-trimethoxy-6-methylnaphthalene 
• 1026004-58-9 8-Benzyloxy-2-bromo-6-methoxy-7-methyl-naphthalene-1,4-diol 
• 165258-04-8 5-(Benzyloxy)-3-bromo-7-methoxy-6-methyl-1,4-naphthoquinone 
• 165258-03-7 3-Bromo-5-hydroxy-7-methoxy-6-methyl-1,4-naphthoquinone 
• 100-39-0 benzyl bromide 
• 165258-12-8 Methyl 5-(benzyloxy)-8-<(4'S,2'E)-5'-(tert-butyldiphenylsiloxy)-2',4'-dimethyl-1'-oxopent-2'-en-1'-yl>-1,4,7-trimethoxy-6-methylnaphth-3-oate 

Downstream Products

• 165258-14-0 5-(Benzyloxy)-8-<(4'S,2'E)-5'-(tert-butyldiphenylsiloxy)-2',4'-dimethyl-1'-oxopent-2'-en-1'-yl>-1,4,7-trimethoxy-6-methyl-3-carbonyl>amino>naphthalene 
• 165258-16-2 8-<(4'S,2'E)-5'-(tert-Butyldiphenylsiloxy)-2',4'-dimethyl-1'-oxopent-2'-en-1'-yl>-5-hydroxy-7-methoxy-6-methyl-3-carbonyl>amino>-1,4-naphthoquinone 

Relevant academic research and scientific papers

Synthesis of the naphthoquinone nucleus of awamycin

A synthesis of ketone 4, corresponding to the fully elaborated naphthoquinone nucleus of awamycin, is described. The synthesis involves the Diels-Alder reaction between diene 8 and quinone 9 to construct naphthoquinone 10, the coupling of bromide 15 and an ansa chain surrogate 17 via an aryllithium intermediate, and a late stage 1,4-addition of NaSMe to naphthoquinone 23 to afford the ketone 4.