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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Asymmetric induction in 8π electrocyclizations. Design of a removable chiral auxiliary
Keunsoo Kim1, Joseph W Lauher, Kathlyn A Parker
1Department of Chemistry, Stony Brook University, Stony Brook, New York 11733, USA.
None:
The pseudo C(2) symmetric trans diphenyl oxazoline group acts as an effective chiral auxiliary in the 8π, 6π tandem electrocyclization of a substituted tetraene 1-carboxylic acid. Assignment of absolute stereochemistry to the [4.2.0] bicyclooctadiene product supports a model in which both s-cis and s-trans conformations favor the transition states with the same helical twist. This assignment prefaces the development of analogs of SNF4435 C and D. These natural products demonstrate activity as androgen receptor antagonists and as multidrug resistance (mdr) reversal agents.
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