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Biomimetic total synthesis of forbesione and desoxymorellin utilizing a tandem Claisen/Diels–Alder/Claisen rearrangement

2003; Royal Society of Chemistry; Volume: 1; Issue: 24 Linguagem: Inglês

10.1039/b311833a

1477-0539

Eric J. Tisdale, Irina Slobodov, Emmanuel A. Theodorakis,

Chemical synthesis and alkaloids

A concise synthesis of forbesione (1) and desoxymorellin (3) is presented. Central to the strategy is a biomimetic Claisen/Diels–Alder/Claisen reaction cascade that proceeds in a regioselective manner and produces the desired scaffold exclusively. The observed regioselectivity and product distribution of the Claisen/Diels–Alder/Claisen reaction are attributed to the electronic effects of the xanthone oxygen (O10), the C9 carbonyl group and the nature of the C1 functionality.