Methods of treating or suppressing mitochondrial diseases, such as Friedreich's ataxia (FRDA), Leber's Hereditary Optic Neuropathy (LHON), mitochondrial myopathy, encephalopathy, lactacidosis, stroke (MELAS), or Kearns-Sayre Syndrome (KSS) are disclosed, as well as compounds useful in the methods of the invention, such as alpha-tocopherol quinone. Methods and compounds useful in treating other disorders are also disclosed. Energy biomarkers useful in assessing the metabolic state of a subject and the efficacy of treatment are also disclosed. Methods of modulating, normalizing, or enhancing energy biomarkers, as well as compounds useful for such methods, are also disclosed.

Methods of treating or suppressing mitochondrial diseases, such as Friedreich's ataxia (FRDA), Leber's Hereditary Optic Neuropathy (LHON), mitochondrial myopathy, encephalopathy, lactacidosis, stroke (MELAS), or Kearns-Sayre Syndrome (KSS) are disclosed, as well as compounds useful in the methods of the invention, such as alpha-tocopherol quinone. Methods and compounds useful in treating other disorders are also disclosed. Energy biomarkers useful in assessing the metabolic state of a subject and the efficacy of treatment are also disclosed. Methods of modulating, normalizing, or enhancing energy biomarkers, as well as compounds useful for such methods, are also disclosed.

Methods of treating or suppressing mitochondrial diseases, such as Friedreich's ataxia (FRDA), Leber's Hereditary Optic Neuropathy (LHON), mitochondrial myopathy, encephalopathy, lactacidosis, stroke (MELAS), or Kearns-Sayre Syndrome (KSS) are disclosed, as well as compounds useful in the methods of the invention, such as alpha-tocopherol quinone. Methods and compounds useful in treating other disorders are also disclosed. Energy biomarkers useful in assessing the metabolic state of a subject and the efficacy of treatment are also disclosed. Methods of modulating, normalizing, or enhancing energy biomarkers, as well as compounds useful for such methods, are also disclosed.

Using a combination of Kumada, Suzuki and Biellmann chemistry, various menaquinones can synthesised rapidly and with stereochemical integrity offering a new way of preparing these vitamin K2 components for the pharmaceutical market. In one embodiment a process for the preparation of a compound of formula (I)

##STR00001## is defined including a step in which (i) a compound of formula (II) is reacted with a compound of formula (III)

##STR00002## wherein R is an alkyl group; LG is a leaving group; m is an integer from 0 to 8; n is an integer of from 0 to 9; and X is hydrogen, halide, hydroxyl or protected hydroxyl; in the presence of a copper, nickel or palladium catalyst.

Using a combination of Kumada, Suzuki and Biellmann chemistry, various menaquinones can synthesised rapidly and with stereochemical integrity offering a new way of preparing these vitamin K2 components for the pharmaceutical market. In one embodiment a process for the preparation of a compound of formula (I)

##STR00001## is defined including a step in which (i) a compound of formula (II) is reacted with a compound of formula (III)

##STR00002## wherein R is an alkyl group; LG is a leaving group; m is an integer from 0 to 8; n is an integer of from 0 to 9; and X is hydrogen, halide, hydroxyl or protected hydroxyl; in the presence of a copper, nickel or palladium catalyst.

Using a combination of Kumada, Suzuki and Biellmann chemistry, various menaquinones can synthesised rapidly and with stereochemical integrity offering a new way of preparing these vitamin K2 components for the pharmaceutical market. In one embodiment a process for the preparation of a compound of formula (I)

##STR00001## is defined including a step in which (i) a compound of formula (II) is reacted with a compound of formula (III)

##STR00002## wherein R is an alkyl group; LG is a leaving group; m is an integer from 0 to 8; n is an integer of from 0 to 9; and X is hydrogen, halide, hydroxyl or protected hydroxyl; in the presence of a copper, nickel or palladium catalyst.

The invention relates to a method and intermediate compounds for the preparation of menaquinone MK-7. The method for the preparation of menaquinone MK-7 is characterized in that, it comprises coupling of a compound of formula (11) with a compound of formula (17) in the presence of a base, to obtain a compound of formula (18), which is subjected to desulfonylation reaction in the presence of a palladium catalyst, to obtain a compound of formula (19), which is subjected to oxidation reaction, to obtain menaquinone MK-7. The invention also relates to compound (8), preferably in a crystalline form, which is a convenient intermediate compound for the preparation of menaquinone MK-7.

The invention relates to a method and intermediate compounds for the preparation of menaquinone MK-7. The method for the preparation of menaquinone MK-7 is characterized in that, it comprises coupling of a compound of formula (11) with a compound of formula (17) in the presence of a base, to obtain a compound of formula (18), which is subjected to desulfonylation reaction in the presence of a palladium catalyst, to obtain a compound of formula (19), which is subjected to oxidation reaction, to obtain menaquinone MK-7. The invention also relates to compound (8), preferably in a crystalline form, which is a convenient intermediate compound for the preparation of menaquinone MK-7.

The invention relates to a method and intermediate compounds for the preparation of menaquinone MK-7. The method for the preparation of menaquinone MK-7 is characterized in that, it comprises coupling of a compound of formula (11) with a compound of formula (17) in the presence of a base, to obtain a compound of formula (18), which is subjected to desulfonylation reaction in the presence of a palladium catalyst, to obtain a compound of formula (19), which is subjected to oxidation reaction, to obtain menaquinone MK-7. The invention also relates to compound (8), preferably in a crystalline form, which is a convenient intermediate compound for the preparation of menaquinone MK-7.

The invention discloses novel processes for production, enrichment and/or isolation of alpha-tocotrienol from source material comprising at least one non-alpha-tocotrienol, such as natural extracts comprising mixed tocotrienols.