Stereodivergent Attached-Ring Synthesis via Non-Covalent Interactions: A Short Formal Synthesis of Merrilactone A
A strategy to control the diastereoselectivity of bond formation at a prochiral attached-ring bridgehead is reported. An unusual stereodivergent Michael reaction relies on basic vs. Lewis acidic conditions and non-covalent interactions to control re- vs. si- facial selectivity en route to fully substituted attached-rings. This divergency reflects differential engagement of one rotational isomer of the attached-ring system. The successful synthesis of an erythro subtarget diastereomer ultimately leads to a short formal synthesis of merrilactone A.
Huffman, Benjamin J., Tiffany Chu, Yusuke Hanaki, et al. 2022. "Stereodivergent Attached-Ring Synthesis via Non-Covalent Interactions: A Short Formal Synthesis of Merrilactone A." Angewandte Chemie-International Edition 61(3): e202114514.
Angewandte Chemie-International Edition
Chemistry and Biochemistry
Attached ring, Diastereoselectivity, Michael addition, Natural productions, Synthesis design