Synthesis of delta-1(9)-octalinols and their analogues

Lupuwana, Lincoln L

Synthesis of delta-1(9)-octalinols and their analogues

Master Thesis

1986

Publisher

University of Cape Town

Department

Department of Chemistry

Faculty

Faculty of Science

Abstract

This project was initiated by the observation that a natural glyeoside of a triterpene, which incorporated the allylic alcoholic moiety 1 gave the novel ketone diene 2 when it was subjected to acetolysis. A number of octahydronaphthalinols (1, R=H) Δ 1 ( 9) octalinols), ' were prepared by reduction of the α, β unsaturated octalones obtained from cyclohexanones condensed with α, β -unsaturated ketones. These octalinols were characterised as their acetates (1, R=Ac). The attempts to convert these to the desired ketone dienes 2 by reaction with mixtures of acetic anhydride-acetic acid-boron trifluoride proved unsuccessful. Two model compounds derived from hecogenin and incorporating the octalinol residue 1 were also prepared in the hope that the analogous ketone 2 might be obtained. This reaction, too, was unsuccessful.

Description

Includes bibliographical references.

Keywords

Organic Chemistry

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