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Synthesis of a 6,11-Dioxa Congener of Torgov's Diene: A Platform Intermediate for Oxasteroid Discovery
Jonathan K Sader1, Jeremy E Wulff1
1Department of Chemistry, University of Victoria, Victoria, British ColumbiaV8W 2Y2, Canada.
Abstract:
We report the de novo synthesis of 6,11-dioxa Torgov's diene, which was accessed via the positional alkene isomerization of an advanced dienone-bearing tetracycle. Other key steps of the synthesis include a Schenck-ene photooxygenation, a cationic annulation reaction, a singlet oxygen-mediated cascade, and a Pd2+-catalyzed Friedel-Crafts cyclization. In addition to 6,11-dioxa Torgov's diene, we accessed a collection of its saturated analogues by applying a set of stereodivergent hydrogenation conditions.
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