Eric Tisdale - Total synthesis of seco-lateriflorone.

Document created by Eric Tisdale on Aug 22, 2014
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  Tisdale, E. J.; Vong, B. G.; Li, H.; Kim, S. H.; Chowdhury, C.;   Theodorakis, E. A. Total synthesis of   seco-lateriflorone. Tetrahedron  2003, 59, 6873-6887.


  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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