CHED 847 |
Progress toward the synthesis of chrolactomycin
| Melissa Beenen, William Morris, and Karl Scheidt. Chemistry, Northwestern University, 2145 Sheridan Rd., Evanston, IL 60208-3113 |
Chrolactomycin (1) is a recently isolated natural product possessing antitumor properties against a spectrum of human tumor cell lines. The interesting biological activity combined with the novel 6-5 fused bicyclic core renders this macrocyclic compound an important synthetic target. The research presented focuses on the eight-step construction of intermediate (2) using iterative diastereoselective Myer’s alkylations and a modified acetoacetate aldol reaction. The resulting ß-keto ester (2) will be incorporated into the molecule in a highly convergent manner by way of a diastereoselective Maitland-Japp reaction with 3 affording the desired pyrone ring and the fully assembled carbon skeleton of chrolactomycin. Further results and progress towards this total synthesis will also be discussed.  |
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