Total synthesis of mono-THF acetogenins

Our synthesis of corossolin started from the cheap sugar material, D-glucono-5-lactone, whose C-3 and C-4 stereogenic centers were introduced into the target as C-19 and C-20, respectively. Subsequent introduction of C-15 and C-16 was achieved by Sharpless epoxidation of an allylic alcohol intermediate, and then the THF core 14 was established through a couple steps of transformations. On 

TABLE 10-1. In Vitro Cytotoxicities Against B16BL6 by (10/ )- and (lOS)-Corossolin 

A series of chiral stannic synthons was developed and applied successfully into the synthesis of acetogenins by Marshall Jiang. In the synthesis of longifolicin 

A similar disconnection strategy was adopted by Dixon et al. in the United Kingdom in the synthesis of muricatetrocin The retro-synthesis disconnected the 

Many naturally occurring l w-THF acetogenins have also been synthesized in recent years. Besides the mono-THF acetogenins, Marshall et al. also successfully applied 

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On basis of this work, we recently completed the total synthesis of five mono-THF acetogenins (Scheme 10-4), 4-deoxyannomonatacin, tonkinecin, ° (10/ )-... 

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

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