267877-02-1Relevant articles and documents
Total synthesis of trunkamide A, a novel thiazoline-based prenylated cyclopeptide metabolite from Lissoclinum sp.
McKeever, Benedict,Pattenden, Gerald
, p. 2713 - 2727 (2007/10/03)
Full details of a total synthesis of the doubly prenylated cyclic peptide trunkamide A of marine origin, and also its C45 epimer, are described.
Total synthesis of the prenylated cyclopeptide trunkamide A, a cytotoxic metabolite from Lissoclinum sp.
McKeever, Benedict,Pattenden, Gerald
, p. 2573 - 2577 (2007/10/03)
A total synthesis of the doubly prenylated cyclic peptide trunkamide A of marine origin, and also its C45 epimer, is described.
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.
