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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

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Abstract

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.

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Details

Item Type: Article
Status: Published
Creators/Authors:
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
URI: http://d-scholarship.pitt.edu/id/eprint/20627

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