192993-16-1

Upstream product

• 36140-19-9 dicyclohexylboron chloride 
• 192993-13-8 (2R)-1-benzyloxy-2-methylhexan-3-one 
• 116652-76-7 (2R)-3-benzyloxy-N-methoxy-N-methyl-2-methylpropanamide 
• 81927-55-1 O-benzyl 2,2,2-trichloroacetimidate 
• 56850-58-9 methyl (2R)-3-(benzyloxy)-2-methylpropanoate 

Downstream Products

• 192993-17-2 (4S,5S,6S)-4-((R)-2-Benzyloxy-1-methyl-ethyl)-2-cyclohexyl-5-ethyl-6-isopropenyl-[1,3,2]dioxaborinane 
• 192993-18-3 (3S,4S,5S,6R)-7-benzyloxy-4-ethyl-2,6-dimethylhept-1-ene-3,5-diol 
• 192993-19-4 (2R,3R,4R,5S,6R)-7-benzyloxy-3,5-(di-tert-butylsilylenedioxy)-4-ethyl-2,6-dimethylheptan-1-ol 
• 192993-21-8 (2R,3R,4R,5S,6R)-3,5-(di-tert-butylsilylenedioxy)-4-ethyl-2,6-dimethyl-1-(2',2'-dimethylpropanoyloxy)-7-(para-tolylsulfonyloxy)heptane 

Relevant academic research and scientific papers

Studies in macrolide synthesis: Stereocontrolled synthesis of a C1-C13 segment of concanamycin A

The C1-C13 segment 6 of concanamycin A (1) was prepared by a highly stereocontrolled route (87% overall ds) in 16 steps from the ester 9. Key steps are the one-pot aldol/reduction, 8 → 12, and the HWE reaction, 18 + 19 → 6.

Stereocontrolled total synthesis of (+)-concanamycin F: The strategic use of boron-mediated aldol reactions of chiral ketones

A highly stereocontrolled total synthesis of the 18-membered macrolide (+)-concanamycin F, a potent inhibitor of vacuolar ATPases, is described that proceeds in 5.8% yield over 26 steps. The three key fragments, C1-C13 vinyl iodide, C14-C22 vinyl stannane