245115-70-2Relevant academic research and scientific papers
Total synthesis and revision of stereochemistry of the marine metabolite trunkamide A
Wipf, Peter,Uto, Yoshikazu
, p. 1037 - 1049 (2007/10/03)
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.
Total synthesis of the putative structure of the marine metabolite trunkamide A
Wipf, Peter,Uto, Yoshikazu
, p. 5165 - 5169 (2007/10/03)
The structure assigned to trunkamide A, a cycloheptapeptide alkaloid isolated from the colonial ascidian Lissoclinum sp., was prepared via segment condensations and an efficient oxazoline-thiazoline interconversion. The novel reverse prenylated serine and
