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Article Abstract
A concise enantioselective total synthesis of (+)-lucidumone, a caged polycyclic meroterpenoid with a bicyclo[2.2.2]octane skeleton, was accomplished in 10 steps (LLS) starting from commercially available 2-cyclohexen-1-one. The key step features a quinine derivative-catalyzed double Michael addition that constructs the essential chiral bicyclo[2.2.2]octane framework with five contiguous stereocenters. Additional features include a Nef reaction and a one-pot Brønsted acid-promoted cyclization, which simultaneously form both Indane and hydrofuran ring systems.
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| http://dx.doi.org/10.1021/acs.orglett.5c03633 | DOI Listing |
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