Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 21, Pages 7107-7112Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201902777
Keywords
anti-Bredt olefins; Bredt rule; bridgehead double bonds; natural products; reassignments
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Funding
- University of Denver
- University of Queensland
- Australian Research Council [FT120100632, DP180103047, FT110100851]
- US National Science Foundation [CHE 1665342]
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Structural misassignments of natural products are prevalent in the literature. Developing methods and theoretical concepts to assist those undertaking structural elucidation is therefore of paramount importance, such that biologists and synthetic chemists avoid pursuing phantom chemical entities. Herein described is a strategy for predicting the isolabilities of oxygen-substituted bridgehead natural products based on calculations of olefin strain energies, NMR chemical shifts and coupling constants (DU8+). This approach provides corroborating evidence for the structures of certain bridgehead alkene natural products while leading to the reassignment of several other structures.
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