Publication Details (including relevant citation information):
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.
Address (URL): http://dx.doi.org/10.1039/b311833a