Mycolipenic acid

Figure 4.22. Natural products synthesized by asymmetric 1,4-addition of cuprates to esters citronellic acid [124] California red scale pheromone [129] mycolipenic acid (W. Oppolzer T. Godel, unpublished, quoted in [130]) the alleged norpectinatone [128] vitamin E side chain (W. Oppolzer R. Moretti, unpublished, quoted in [ 130]) southern com rootworm pheromone...

Wallace, P.A., and D.E. Minnikin, Synthesis of a Derivative of Racemic 3-Hydroxy-2,4,6-trimethyltetracosanoic (Mycohpanolic) Acid and Racemic 2,4,6-Trimethyltetraco-2-enoic (Mycolipenic) Acid, Chem. Phys. Lipids 83 1-8 (1996). 

Mycolipenic acid. C27-Phthienoic acid Constit. of lipids of tubercle bacilli. Cryst. (Mc2CO at -8°). Mp 28°. [a]2jJ +19.3° (c, 3.0 in CHCI3). Racemic and opt. active stereoisomers have been synthesised. 

Mycolipenic acid, in T-00212 Mycolipodienic acid, M-00132 >Mycomycin, see T-OOl 57 a-Myrcenc, see M-00072 Myricyl alcohol, see T-OOl 14 >Myristaldehydc, see T-00029 >Myristic acid, see T-00034 >Myristic aldehyde, see T-00029 Myristoleic acid, in T-00060 Myristoylpalmitoylphosphatidylcholine, see G-00235... 

Note that, particularly in micro-organisms and insects, methyl-malonate (equivalent to a propionic acid unit) can replace malonate (resulting in an acetate unit) in the condensation reaction to give a polyketide. Mycolipenic acid contains three propionate units and nine acetate units, erythromycin is made from seven propionates (Figure 4.7). 

Figure 4.7 Acetogenin structures containing propionate units. Mycolipenic acid is...

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