Studies towards the total synthesis of taxol. Synthesis of A-ring intermediate with all the latent functionalities.

Title: Studies towards the total synthesis of taxol. Synthesis of A-ring intermediate with all the latent functionalities.
Identifier: AAI9108166
identifier: 9108166
Creator: Rao, Meenakshi Srikumar.
Contributor: Adviser: William F. Berkowitz
Date: 1990
Language: English
Publisher: City University of New York.
Subject: Chemistry, Organic | Chemistry, Pharmaceutical
Abstract: Taxol (1) belongs to a class of compounds called taxanes, which are diterpenoids isolated from the plants of the family taxaceae. It has potent antileukemic and tumor inhibiting properties.(DIAGRAM, TABLE OR GRAPHIC OMITTED...PLEASE SEE DAI).;Methods for the synthesis of ethyl 2,6,6-trimethylcylohexen-5-one carboxylate, a key synthon for its total synthesis were investigated. Robinson anulation was found to be the most effective of these methods, and was applied to obtain this compound.;The allylic alcohol alcohol resulting from the grignard reaction of isobutyraldehyde and vinyl magnesium bromide was oxidized to isopropyl vinyl ketone. Michael addition of diethyl oxalpropionate to this followed by acid catalyzed aldol condensation gave a hydroxy ester, which was dehydrated to give the required compound.
Type: dissertation
Source: PQT Legacy CUNY.xlsx
degree: Ph.D.

Media: Studies towards the total synthesis of taxol. Synthesis of A-ring intermediate with all the latent functionalities.