THE CONVERSION OF LOGANIN TO AN ANALOG OF PROSTAGLANDIN INTERMEDIATE.

Title: THE CONVERSION OF LOGANIN TO AN ANALOG OF PROSTAGLANDIN INTERMEDIATE.
Identifier: AAI8708270
identifier: 8708270
Creator: ARAFAT, ABDEL-FATTAH MOUSTAFA.
Contributor: William F. Berkowitz
Date: 1987
Language: English
Publisher: City University of New York.
Subject: Chemistry, Organic
Abstract: The prostaglandin analog intermediate 23a, has been prepared from Loganin 1. The enol ether system of the pentaacetate of this iridoid 2 was oxidized to the corresponding lactone 11. Ring opening, glucose cleavage and decarboxylation of this lactone was accomplished in one pot to give the key intermediate aldehyde-ester 13, in good yield. Wadsworth-Emmons reaction of 13 gave the desired prostanoid-like trans 23 in 81% yield. The phosphonate reagent 22 was prepared in a two step reaction in 76% yield. Several.;other potential intermediates were also prepared from loganin in particular, compounds 6 and 7.;*Please see dissertation for diagrams.
Type: dissertation
Source: PQT Legacy CUNY.xlsx
degree: Ph.D.
Program: Chemistry

Media: THE CONVERSION OF LOGANIN TO AN ANALOG OF PROSTAGLANDIN INTERMEDIATE.