Synthetic studies related to the marine natural product oscillatoxin D
Osdllatoxin D is a nontoxic natural product found in tropical marine bluegreen algae which possesses antileukemic activity. This dissertation describes progress towards the synthesis of structurally advanced intermediates for the total synthesis of osdllatoxin D. The overall goal of this research is to test synthetic methodology aimed at streamlining the synthesis of advanced intermediates. This goal was achieved through several objectives. First, attempts were made o resolve antidpated problems with the introduction of y-lactone portion of osdllatoxin D. during the synthesis by the exploration of a novel carboxylic acid protection groups which could be removed under mild conditions. Second, attempts were made to improve the efficiency of a previously described synthesis of a major intermediate for the synthesis of osdllatoxin D. Third, an osdllatoxin D precursor bearing all of the carbon atoms of osdllatoxin D itself was prepared and used to test a hypothetical spirobicyclization reaction which would, if successful, have formed the complete central bicydic portion of osdllatoxin D.