Heteroatom-directed Wacker oxidations. A protection-free synthesis of (-)-heliophenanthrone.


The first enantioselective six-step synthesis of (-)-heliophenanthrone has been achieved without any protection-deprotection protocol at an overall yield of 28%. Key features of this synthesis comprise a heteroatom-directed Wacker oxidation of an internal cyclic olefin in addition to asymmetric Brown allylation and ring closing metathesis (RCM). 
DOI: 10.1039/c2ob07095b


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