Abstract
(Chemical Equation Presented) A stereoselective synthesis of the BCDE fragment of brevetoxin A has been completed. anti-Glycolate aldol, glycolate alkylation, and ring-closing metathesis reactions were employed as key bond-forming events. A convergent assembly strategy was employed that relied on a Horner-Wadsworth-Emmons union of two complex fragments. Subsequent cyclization and dehydration led to efficient generation of an intermediate endocyclic enol ether, which was advanced to a tetracyclic fragment.
| Original language | English |
|---|---|
| Pages (from-to) | 4033-4036 |
| Number of pages | 4 |
| Journal | Organic Letters |
| Volume | 7 |
| Issue number | 18 |
| DOIs | |
| State | Published - 1 Sep 2005 |
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Crimmins, M. T., McDougall, P. J., & Emmitte, K. A. (2005). A convergent coupling strategy for the formation of polycyclic ethers: Stereoselective synthesis of the BCDE fragment of brevetoxin A. Organic Letters, 7(18), 4033-4036. https://doi.org/10.1021/ol051543m