Title page for ETD etd-050505-131337

Document Type thesis

Author Name White, Rachael A

URN etd-050505-131337

Title Asymmetric Synthesis of Prostaglandins

Degree MS

Department Chemistry & Biochemistry

Advisors
J. P. Dittami, Advisor

Keywords
prostaglandins
organic synthesis

Date of Presentation/Defense 2005-05-05

Availability unrestricted

Abstract
Prostaglandins (PGs) are medicinally interesting because of the wide variety of roles they play in the body. PGs are ubiquitous and can be found in the reproductive system, the nervous system, the cardiovascular system, and the immune system. Accordingly, PGs are an important therapeutic target for pharmaceutical companies, and an efficient synthesis is highly desirable. Past research indicates that an approach to prostaglandins via a chiral acetylenic ester or amide provides a promising method for control of C-15 geometry. This project seeks to validate a key stereospecific reduction of an enantiomerically pure cyclopentenone intermediate. This is in turn available from a chiral acetylenic ester or amide via a formal [3+2] cycloaddition step. Several methods have been investigated for asymmetric synthesis of the requisite chiral acetylenic acid derivative including asymmetric conjugate addition, CBS-oxazaborolidine reduction of a ketone, and the separation of diastereomers of a chiral amide. With the optically pure cyclopentenone in hand, we will investigate hydroxyl directed conjugate reduction of the cyclopentenone double bond.

Files
rwhite.pdf

Browse by Author | Browse by Department | Search all available ETDs

Questions? Email etd-questions@wpi.edu
Maintained by webmaster@wpi.edu

Document Type	thesis
Author Name	White, Rachael A
URN	etd-050505-131337
Title	Asymmetric Synthesis of Prostaglandins
Degree	MS
Department	Chemistry & Biochemistry
Advisors	J. P. Dittami, Advisor
Keywords	prostaglandins organic synthesis
Date of Presentation/Defense	2005-05-05
Availability	unrestricted
Abstract Prostaglandins (PGs) are medicinally interesting because of the wide variety of roles they play in the body. PGs are ubiquitous and can be found in the reproductive system, the nervous system, the cardiovascular system, and the immune system. Accordingly, PGs are an important therapeutic target for pharmaceutical companies, and an efficient synthesis is highly desirable. Past research indicates that an approach to prostaglandins via a chiral acetylenic ester or amide provides a promising method for control of C-15 geometry. This project seeks to validate a key stereospecific reduction of an enantiomerically pure cyclopentenone intermediate. This is in turn available from a chiral acetylenic ester or amide via a formal [3+2] cycloaddition step. Several methods have been investigated for asymmetric synthesis of the requisite chiral acetylenic acid derivative including asymmetric conjugate addition, CBS-oxazaborolidine reduction of a ketone, and the separation of diastereomers of a chiral amide. With the optically pure cyclopentenone in hand, we will investigate hydroxyl directed conjugate reduction of the cyclopentenone double bond.
Files	rwhite.pdf