Synthesis of the ABC framework of tamulamides A and B
Author(s)Kelley, Elizabeth H. (Elizabeth Helen); Jamison, Timothy F
MetadataShow full item record
Synthesis of the fused tetrahydrofuran motif comprising the ABC rings of the marine ladder polyethers tamulamides A and B has been achieved via two different polyepoxide cascade strategies. Investigations into a triepoxide cascade under aqueous conditions revealed the importance of the electronic nature of the cascade end-group with this initial approach. Ultimately, a diepoxide cascade under basic conditions proved most successful, providing the ABC tetrahydropyran triad in 41% yield.
Part of special issue: Symposium in Print in honour of Laura Kiessling, Tetrahedron Prize for Creativity in Organic Chemistry 2017.
DepartmentMassachusetts Institute of Technology. Department of Chemistry
Bioorganic & Medicinal Chemistry
Kelley, Elizabeth H., and Timothy F. Jamison, "Synthesis of the ABC framework of tamulamides A and B." Bioorganic & Medicinal Chemistry 26, 19 (Oct. 2018): 5327-35 doi 10.1016/J.BMC.2018.04.046 ©2018 Author(s)
Author's final manuscript