Alexandria Digital Research Library

Developments of New Reactions in Enolate Chemistry Inspired by the Total Synthesis of Bioactive Marine Natural Products

Author:
Stivala, Craig Evan
Degree Grantor:
University of California, Santa Barbara. Chemistry
Degree Supervisor:
Armen Zakarian
Place of Publication:
[Santa Barbara, Calif.]
Publisher:
University of California, Santa Barbara
Creation Date:
2012
Issued Date:
2012
Topics:
Chemistry, General and Chemistry, Organic
Keywords:
Total Synthesis
Stereoselective Alkylation
Ireland-Claisen Rearrangement
Natural Products
Stereoselective Enolization
Genres:
Dissertations, Academic and Online resources
Dissertation:
Ph.D.--University of California, Santa Barbara, 2012
Description:

Marine natural products have long served as leading compounds for new therapeutic agents; however, their utilization is often extremely limited due to poor availability from their natural sources. Therefore, exploration of new synthetic techniques offers shortcuts in the production of such agents and the opportunity to improve the current state of the art. Studies directed toward the synthesis of these biologically active marine natural products inspire the development of new, efficient, economical, and environmentally friendly methods that are broadly useful for the synthesis of new pharmaceuticals and organic compounds for medicinal research.

The development of a wide range of new and exciting chemical transformations revolving around the rich chemistry of enolates is described. Specifically these studies include: 1) a stereoselective enolization of alpha-branched esters, 2) a diastereoselective Ireland-Claisen rearrangement, 3) the stereoselective formation of quaternary stereocenters, and 4) an asymmetric alkylation.

Additionally, the total synthesis of the marine natural products (+)-pinnatoxin A and (+)-pinnatoxin G will be discussed in detail. The diastereoselective Ireland-Claisen rearrangement is a featured method for the stereoselective installation of the quaternary stereocenter in the pinnatoxins and other related spiroimine natural products.

Physical Description:
1 online resource (581 pages)
Format:
Text
Collection(s):
UCSB electronic theses and dissertations
ARK:
ark:/48907/f3t151kh
ISBN:
9781267294890
Catalog System Number:
990037519240203776
Rights:
Inc.icon only.dark In Copyright
Copyright Holder:
Craig Stivala
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