Herein, we describe the enantioselective construction of the 12-membered macrocyclic pyrrole core of marineosin A in 5.1% overall yield from ()-propylene oxide. The route features a key Stetter reaction to install a 1,4-diketone, which is then subjected to Paal-Knorr pyrrole synthesis and ring closing metathesis (RCM) to afford macrocycle A divergence point in the synthetic scheme also enabled access to a highly functionalized spiroaminal model system via an acid-mediated hydroxyketoamide cyclization strategy.
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| http://dx.doi.org/10.1002/ejoc.201300643 | DOI Listing |
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