Item – Theses Canada

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OCLC number
1006913734
Link(s) to full text
LAC copy
LAC copy
Author
Robichaud, Joël,1974-
Title
Total synthesis of dysidiolide, ent-dysidiolide, and luffariellolide.
Degree
M. Sc. -- Université Laval, 1999
Publisher
Ottawa : National Library of Canada = Bibliothèque nationale du Canada, [2001]
Description
2 microfiches
Notes
Includes bibliographical references.
Abstract
In the first part of this thesis we describe an enantioselective, convergent total synthesis of the Caribbean sponge constituent dysidiolide (), a novel antitumor sesterterpenoid that is the first reported natural product to inhibit the recently discovered phosphatase Cdc25A. Blocking this enzyme, which plays a key role in the cell cycle, may provide a new means for the treatment of cancer. This formidable combination of novel structure and highly sought biological properties makes dysidiolide an eminent target for synthesis. Our first route to dysidiolide (longest linear sequence = 15 steps, overall yield = 5.3%), published at about the same time as the syntheses of E. J. Corey and S. J. Danishefsky, allowed the absolute configuration of the natural product to be established. More recently, a substantially improved version of our initial route was developed. In the second part of this thesis we detail a highly convergent total synthesis of the anti-inflammatory marine natural product luffariellolide. (Abstract shortened by UMI.)
ISBN
0612420019
9780612420014