ORGN 670 |
Efforts toward a total synthesis of oocydin A (haterumalide NA)
| Thomas R. Hoye and Jizhou Wang. Department of Chemistry, University of Minnesota, 207 Pleasant Street, SE, Minneapolis, MN 55455 |
Oocydin A (haterumalide NA), a potent anti-fungal and cytotoxic agent, has been isolated, now, from two related bacteria (Serratia marcescens and Serratia plymuthica) and from an unrelated Okinawan sponge. Questions about both relative and absolute configuration of the natural product remain. The key reactions in our synthetic efforts to date include the [2+3] cyclization between the secondary allylic silane and aldehyde partners (a la Roush), a palladium-catalyzed chloroallylation to set the Z-chloroalkene geometry (a la Kaneda), and a Tamao oxidation under Woerpel conditions. RCM and RRCM (relay ring-closing metathesis) are being studied to close the 14-membered macrolactone.  |
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