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

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.

Grantor dc:publisher.institution

Department of Chemistry

Year dc:date.issued

1986

Author dc:creator

• Lupuwana, Lincoln L

Advisor dc:contributor.advisor

• Elsworth, J F

Language dc:language.iso

eng

Handle dc:identifier.uri

http://hdl.handle.net/11427/16406

OAI identifier oai:identifier

oai:open.uct.ac.za:11427/16406