%0 Journal Article
%@ 0022-3263
%A Wipf, P
%A Uto, Y
%D 2000
%F pittir:20627
%J Journal of Organic Chemistry
%N 4
%P 1037 - 1049
%T Total synthesis and revision of stereochemistry of the marine metabolite trunkamide A
%U http://d-scholarship-dev.library.pitt.edu/20627/
%V 65
%X The isolation of the cytotoxic Lissoclinum sp. metabolite trunkamide A was reported in 1996. After completion of a total synthesis in 1999, it became clear that the structure of this marine natural product had to be revised. We now report the first preparation of actual trunkamide A in a total synthesis that serves as an unambiguous structural and stereochemical proof. Highlights of our synthetic strategy are a Lewis acid assisted aziridine opening that was used for the preparation of the novel reverse- prenylated serine and threonine side chains as well as an efficient oxazoline-thiazoline interconversion on the macrocyclic skeleton. In addition, several stereoisomers prepared by complementary synthetic protocols serve to illustrate the general scope of our methodology and confirm the configurational assignment.