TY  - JOUR
ID  - pittir20627
UR  - http://d-scholarship-dev.library.pitt.edu/20627/
IS  - 4
A1  - Wipf, P
A1  - Uto, Y
Y1  - 2000/02/25/
N2  - 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.
JF  - Journal of Organic Chemistry
VL  - 65
SN  - 0022-3263
TI  - Total synthesis and revision of stereochemistry of the marine metabolite trunkamide A
SP  - 1037 
AV  - public
EP  -  1049
ER  -