Polyprenyl quinol

The reaction has been applied for the synthesis of polyprenyl quinol natural product ubiquinone and vitamin K. 

Chemistry. A new method has been described for the regio- and stereo-controlled polyprenylation of quinones by means of trimethyltin derivatives. The polyprenyl trimethylstannanes (200) were prepared from the polyprenyl halides (201) and trimethylstannyl-lithium, and were then coupled with the required benzo-quinone (202) or naphthoquinone (203) in the presence of BFs-ether to give a quinol which was reduced with Ag20 to the ubiquinone (204) or vitamin K... 

Fig. 15.2 (continued) (26) 2-polyprenyl-6-methoxyphenol (27) 2-polyprenyl-6-metho3iy-l,4-benzo-quinol (28) 2-polypienyl-3-methyl-6-methoxy-l,4-benzoquinol (29) 2-polyprenyl-3-methyl-5-hydroxy-6-methoxy-l,4-benzoquinol (30) ubiquinol (31) ubiquinone (CoQn). Abbreviations ATP adenosine triphosphate, AMP adenosine monophosphate, NADPH/NADP nicotinamide adenine dinucleotide phosphate, CTP cytidine triphosphate, CMP cytidine monophosphate, reduced/oxidized ferredoxin, SAM S -adenosyhnethionine, SAH 5-adenosylhomocysteine... 

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