286853-92-7

Upstream product

• 286854-02-2 (1R,2'R,2''R,5'R,5''R)-1-[5'-(5''-(tert-butyldimethylsilyloxy)methyltetrahydrofuran-2''-yl)tetrahydrofuran-2'-yl]-1-(tert-butyldimethylsilyloxy)-15-benzyloxypentadecan-1-one 

Downstream Products

• 286853-93-8 (1'''R,2'R,2''R,5'R,5''R)-[5-(5'-(1'''-tert-butyldimethylsilyloxy-15'''-benzyloxypentadec-1'''-yl)tetrahydrofuran-2''-yl)tetrahydrofuran-2'-yl]carbaldehyde 
• 286854-06-6 (2R,5R,2'R,5'R)-5'-[(R)-15-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-pentadecyl]-5-[(1S,5S)-1,5-bis-(tert-butyl-dimethyl-silanyloxy)-undecyl]-octahydro-[2,2']bifuranyl 
• 286854-03-3 (1R,2'R,5'R,2''R,5''R,1'''R,5'''S)-1-[5'-(5''-(1''',5'''-bis(tert-butyldimethylsilyloxy)undec-1'''-yl)tetrahydrofuran-2''-yl)tetrahydrofuran-2'-yl]-1-(tert-butyldimethylsilyloxy)-15-benzyloxypentadecane 
• 247586-74-9 (1S,5S,2'R,5'R,2''R,5''R,1'''R)-1-[5'-(5''-(1'''-tert-butyldimethylsilyloxy-15'''-benzyloxypentadec-1'''-yl)tetrahydrofuran-2''-yl)tetrahydrofuran-2'-yl]-5-(tert-butyldimethylsilyloxy)undecan-1-ol 
• 247586-73-8 (1R,5S,2'R,5'R,2''R,5''R,1'''R)-1-[5'-(5''-(1'''-tert-butyldimethylsilyloxy-15'''-benzyloxypentadec-1'''-yl)tetrahydrofuran-2''-yl)tetrahydrofuran-2'-yl]-5-(tert-butyldimethylsilyloxy)undecan-1-ol 
• 156199-51-8 asiminacin 
• 120298-30-8 squamocin 

Relevant academic research and scientific papers

Total Syntheses of Squamocin A and Squamocin D

The total syntheses of two acetogenins, squamocin A and squamocin D, have been achieved. The adjacent bis-THF subunit was constructed by a multiple Williamson reaction. The left and the right side chain were added by addition of organomagnesium compounds to aldehyde functions. The conversion of a carboxylic acid into the butenolide moiety concluded both syntheses.

Total syntheses of squamocin A and squamocin D, bi-tetrahydrofuran acetogenins from Annonaceae

The total syntheses of the Annonaceous acetogenins squamocin A and squamocin D have been achieved. The synthesis follows a modular strategy, wherein a left-side chain, the central bis-THF core and the right-side chain are assembled together. Key reactions are additions of organomagnesium compounds to bi-THF aldehydes. At the end of the synthesis the butenolide moiety was introduced. This modular synthetic approach should be useful for the synthesis of other related natural products as well as pharmacologically interesting analogs.