Access to 2-Oxabicyclo[2.1.1]hexanes and their use in Scaffold Hopping
Olivier Lorthioir1, Niall Anderson1, Scott Boyd1
1Oncology Medicinal Chemistry, R&D AstraZeneca, The Discovery Centre (DISC), Biomedical Campus, 1 Francis Crick Ave, Trumpington, Cambridge CB2 0AA, U.K.
Abstract:
Saturated isosteres of the ortho-substituted benzene ring remain rare due to the paucity of methods to access complex bridged systems. Using blue-light-mediated [2 + 2] photocycloaddition chemistry, we have developed a quick and practical route to provide novel 2-oxabicyclo[2.1.1]hexanes from simple feedstock materials in only three steps. Matched pair analysis confirmed that this motif could prove useful in the future to the drug discovery community as a scaffold endowed with remarkable properties.
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