ORGN 436 |
| Lijun Wang and Paul E. Floreancig. Department of Chemistry, University of Pittsburgh, 219 Parkman Ave, Pittsburgh, PA 15260 |
| Integramycin, isolated in 2002 from Actinoplanes sp by Singh et al, inhibits HIV-1 integrase with an IC50 value of 4 ¦ÌM. In consideration of its biological activity and novel hexacyclic structure, we have initiated efforts toward the total synthesis of integramycin. The A-C rings of integramycin have been synthesized in our group in an efficient and convergent manner through a sequence that employs asymmetric crotylation, olefin hydrocarboxylation, and pseudoephedrine enolate alkylation. A one-pot construction of the spiroketal by the addition of a C,O-dianionic species into lactone avoided extensive protecting group manipulations. Efforts to synthesize the D-F rings of integramycin and to finish the total synthesis will be discussed. |
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Total Synthesis, Asymmetric Reactions and Syntheses, Bioorganic
9:00 AM-11:00 AM, Wednesday, March 31, 2004 Anaheim Convention Center -- Hall C, Poster
Sci-Mix
Division of Organic Chemistry |
