Reticulatacin

Total synthesis of solamin and reticulatacin, two mono-THF acetogenins, confirms their absolute configuration. 

Further efforts by several groups have resulted in total syntheses of muricatacin 38,6, 42-44 (-)-bullatacin (41) (the enantiomer of the natural product), solamin 42, and reticulatacin 24, (Figure 22). All of the above have been synthesized by methods that establish unambiguously their absolute configuration. All of the stereochemical information obtained so far by total synthesis is in complete agreement with the conclusions reached earlier by the methods described in this chapter. 

Tam et al. (14) have reported the hemi-synthesis of reticulatacin 154 from dieporeticanin 157, but by treatment with 70 % perchloric acid. Here again, two compounds 154 and 158 were expected with identical relative configuration, but with opposite absolute configuration across the THF ring, because of the opening arising either at C-17 or C-22 (Fig. 25). 

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