Publication Details (including relevant citation information):
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.
Address (URL): http://dx.doi.org/10.1016/S0040-4020(03)00862-7