Method of preparation of stereospecific quinone derivatives
OwnerDilip S. Mehta, Priya Mohan +2inventors
InventorsDilip S. Mehta, Priya Mohan, Mayank Shastri, Ted Reid
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Abstract
The description provides processes for the regio and stereospecific synthesis of polyprenylatedquinone derivatives, such as Vitamin K1, K2 and Ubiquinone, exploiting dithioacetals, especially 1,3-dithiane, mediated Umpolung chemistry which works along a new concept “Inhibiting resonance delocalization (IRD)” to overcome isomerization generated due to delocalization of allyliccarbanion on the π-electron cloud of an allylic systems by the conventional synthesis.
Claims2
A method for synthesis of polyprenylated quinone derivatives comprising regiospecific and stereospecific synthesis of compound of formula I
- wherein n=an integer from 0 to 8,
- R=is independently selected from —CH═CH—CH═CH—, wherein both R groups form a naphthalene ring and OCH3;
- and
- the said method comprising the steps of providing a dithioacetal derivative selected from the group of quinones (II), prenols (V) and combinations thereof,
- wherein m=2 or 3;
- n=is an integer from 0 to 8;
- R=—CH═CH—CH═CH—, wherein both R groups form a naphthalene ring or OCH3
- R1=CH2OCH3, TMS, TBS, Acetyl, Benzyl, or PMB;
- and
- R2=Et or Ph;
- the said derivatives participating in a reaction with halides of respective counter synthon of formula III or IV,
- wherein R=—CH═CH—CH═CH—, wherein both R groups form a naphthalene ring or OCH3;
- R1=CH2OCH3, TMS, TBS, Acetyl, Benzyl, or PMB;
- and
- X=OMs, Br, Cl, I, OTs.
Dependencies are inferred from the claim text.