Eric Tisdale - Biomimetic total synthesis of forbesione and desoxymorellin utilizing a tandem Claisen/Diels-Alder/Claisen rearrangement.

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  Tisdale, E. J.; Slobodov, I.; Theodorakis, E. A. Biomimetic total   synthesis of forbesione and desoxymorellin utilizing a tandem   Claisen/Diels-Alder/Claisen rearrangement. Org. Biomol.   Chem. 2003, 1, 4418-4422.


  A concise synthesis of forbesione and desoxymorellin 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.

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