Link to the University of Pittsburgh Homepage
Link to the University Library System Homepage Link to the Contact Us Form

Total synthesis and revision of stereochemistry of the marine metabolite trunkamide A

Wipf, P and Uto, Y (2000) Total synthesis and revision of stereochemistry of the marine metabolite trunkamide A. Journal of Organic Chemistry, 65 (4). 1037 - 1049. ISSN 0022-3263

[img] Plain Text (licence)
Available under License : See the attached license file.

Download (1kB)


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.


Social Networking:
Share |


Item Type: Article
Status: Published
CreatorsEmailPitt UsernameORCID
Wipf, Ppwipf@pitt.eduPWIPF
Uto, Y
Date: 25 February 2000
Date Type: Publication
Journal or Publication Title: Journal of Organic Chemistry
Volume: 65
Number: 4
Page Range: 1037 - 1049
DOI or Unique Handle: 10.1021/jo9914566
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 0022-3263
MeSH Headings: Alkaloids--chemical synthesis; Alkaloids--chemistry; Animals; Magnetic Resonance Spectroscopy; Mass Spectrometry; Molecular Structure; Peptides, Cyclic--chemical synthesis; Peptides, Cyclic--chemistry; Stereoisomerism; Urochordata--chemistry
PubMed ID: 10814052
Date Deposited: 27 Feb 2014 16:51
Last Modified: 02 Feb 2019 15:57


Monthly Views for the past 3 years

Plum Analytics

Actions (login required)

View Item View Item