ArticleThe Journal of antibiotics2019
Sequential exo-mode oxacyclizations for the synthesis of the CD substructure of brevenal.
Article in The Journal of antibiotics, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.
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Abstract
We describe a novel strategy for synthesizing the CD bicyclic ether substructure of the fused polycyclic ether natural product brevenal. This product arises from a three-step sequence beginning with (1) regio- and diastereoselective iodoetherification of an acyclic diene-diol, followed by (2) alkene metathesis with an epoxyalkene synthon, concluding with (3) palladium-catalyzed cycloisomerization. Despite the modest yield and long reaction period for the cycloisomerization step, these studies provide valuable insights into the nature of byproducts generated and the mechanisms by which they form. This work demonstrates a portion of a larger synthetic strategy for constructing the pentacyclic core of brevenal from an acyclic precursor.
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