Patent ID: 7572606

Claim:
A method of producing a first compound of Formula I, wherein the dashed lines represent a single or a double bond, wherein R 1 is separately selected from the group consisting of a hydrogen, a halogen, mono-substituted, poly-substituted or unsubstituted variants of the following residues: saturated C 1 -C 24 alkyl, unsaturated C 2 -C 24 alkenyl or C 2 -C 24 alkynyl, acyl, acyloxy, alkyloxycarbonyloxy, aryloxycarbonyloxy, cycloalkyl, cycloalkenyl, alkoxy, cycloalkoxy, aryl, heteroaryl, arylalkoxy carbonyl, alkoxy carbonylacyl, amino, aminocarbonyl, aminocarboyloxy, nitro, azido, phenyl, cycloalkylacyl, hydroxy, alkylthio, arylthio, oxysulfonyl, carboxy, cyano, and halogenated alkyl including polyhalogenated alkyl, where n is equal to 1 or 2, and if n is equal to 2, then R 1 can be the same or different; wherein R 2 is selected from the group consisting of hydrogen, a halogen, mono-substituted, poly-substituted or unsubstituted variants of the following residues: saturated C 1 -C 24 alkyl, unsaturated C 2 -C 24 alkenyl or C 2 -C 24 alkynyl, acyl, acyloxy, alkyloxycarbonyloxy, aryloxycarbonyloxy, cycloalkyl, cycloalkenyl, alkoxy, cycloalkoxy, aryl, heteroaryl, arylalkoxy carbonyl, alkoxy carbonylacyl, amino, aminocarbonyl, aminocarboyloxy, nitro, azido, phenyl, cycloalkylacyl, hydroxy, alkylthio, arylthio, oxysulfonyl, carboxy, cyano, and halogenated alkyl including polyhalogenated alkyl; wherein R 3 is selected from the group consisting of a halogen, mono-substituted, poly-substituted or unsubstituted variants of the following residues: saturated C 1 -C 24 alkyl, unsaturated C 2 -C 24 alkenyl or C 2 -C 24 alkynyl, acyl, acyloxy, alkyloxycarbonyloxy, aryloxycarbonyloxy, cycloalkyl, cycloalkenyl, alkoxy, cycloalkoxy, aryl, heteroaryl, arylalkoxy carbonyl, alkoxy carbonylacyl, amino, aminocarbonyl, aminocarboyloxy, nitro, azido, phenyl, cycloalkylacyl, hydroxy, alkylthio, arylthio, oxysulfonyl, carboxy, cyano, and halogenated alkyl including polyhalogenated alkyl; wherein each of E 1 , E 2 , E 3 and E 4 is a substituted or unsubstituted heteroatom; the method comprising culturing a strain of Salinospora in a saline medium using a feedstock that is deficient in or has an excess of one or more of proprionate, butyrate, or valerate compared to levels of proprionate, butyrate, and valerate found in a medium comprising starch, Hy soy, and yeast in a ratio of 10 g to 4 g to 4 g such that the relative yield of the first compound in comparison to the yield of a second compound of Formula I is substantially different than the relative yield of the first compound in comparison to the yield of the second compound obtained when the strain is cultured in a medium comprising starch, Hy soy, and yeast in a ratio of 10 g to 4 g to 4 g.