THE CONVERSION OF THE IRIDOID AUCUBIN TO A CHIRAL PROSTANOID SYNTHON.

Title: THE CONVERSION OF THE IRIDOID AUCUBIN TO A CHIRAL PROSTANOID SYNTHON.
Identifier: AAI8212209
identifier: 8212209
Creator: PIERCE, DAVID RODNEY.
Contributor: William F. Berkowitz
Date: 1982
Language: English
Publisher: City University of New York.
Subject: Chemistry, Organic
Abstract: The iridoid aucubin has been converted to good yield to a potential intermediate in the synthesis of prostaglandins and prostanoids, particularly those having an 11-deoxy-11-hydroxymethyl substituent. This has been achieved by converting aucubin to its hexaacetate, and hydrogenating the latter with rhodium on carbon in ethyl acetate to give the (beta)-isomer of tetrahydroaucubin hexaacetate. Hydrolysis of this compound to the hemiacetal (the preferred structure for the hydroxyaldehyde) was achieved by a two step procedure through the hemithioacetal.
Type: dissertation
Source: PQT Legacy CUNY.xlsx
degree: Ph.D.
Program: Chemistry

Media: THE CONVERSION OF THE IRIDOID AUCUBIN TO A CHIRAL PROSTANOID SYNTHON.