Studies directed toward the total synthesis of gascardic acid

Brown, William Larry (1984) Studies directed toward the total synthesis of gascardic acid. Masters thesis, Memorial University of Newfoundland.

[img] [English] PDF (Migrated (PDF/A Conversion) from original format: (application/pdf)) - Accepted Version
Available under License - The author retains copyright ownership and moral rights in this thesis. Neither the thesis nor substantial extracts from it may be printed or otherwise reproduced without the author's permission.

Download (9Mb)
  • [img] [English] PDF - Accepted Version
    Available under License - The author retains copyright ownership and moral rights in this thesis. Neither the thesis nor substantial extracts from it may be printed or otherwise reproduced without the author's permission.
    (Original Version)

Abstract

Various reactions directed toward the total synthesis of gascardic acid have been delineated. Unfortunately trisubstituted cyclopentadienes of type 31a and 31b would not partake in the desired intramolecular Diels-Alder reactions. In contrast, compounds 68 and 73 in which the sidechain substituents differ, cyclized to the requisite tricyclic skeletons. -- A general method for inverting the stereochemistry of vinyl alcohols such as 20 and 37 has been developed. This involved a [2,3] sulfoxide rearrangement and will permit a broader application of the oxy-Cope rearrangement as illustrated by the conversion of 37 to 53 to 54. -- Model studies of a suitable cyclohexane-cycloheptane ring expansion in which the keto-ester functionality is retained were commenced.

Item Type: Thesis (Masters)
URI: http://research.library.mun.ca/id/eprint/4228
Item ID: 4228
Additional Information: Bibliography: leaves 82-84.
Department(s): Science, Faculty of > Chemistry
Date: 1984
Date Type: Submission
Library of Congress Subject Heading: Gascardic acid; Sesterterpenes

Actions (login required)

View Item View Item

Downloads

Downloads per month over the past year

View more statistics