Rearrangements of unnatural steroids

Type of content
Theses / Dissertations
Publisher's DOI/URI
Thesis discipline
Chemistry
Degree name
Master of Science
Publisher
University of Canterbury. Chemistry
Journal Title
Journal ISSN
Volume Title
Language
Date
1971
Authors
Muir, C. N.
Abstract

Part I. 3α-Hydroxy-5,6α-epoxy-cholestane (1d)¹ and 3β-hydroxy-5,6β-epoxy-cholestane (2b) have been reacted with BF₃-etherate in benzene. The 3α-hydroxy-(2c) and the 3α-acetoxy-(2e) 5,6β-epoxy-cholestanes¹ have been prepared and their reactions on treatment with BF₃-etherate examined. Part II. 3β,6β-diacetoxy-5α-hydroxy-9β-cholestane (73a) and 3β,5α,6β-triacetoxy-9β-cholestane (74) have been prepared, and reacted with H₂SO₄-Ac₂O-AcOH² and BF₃-etherate-Ac₂O respectively. The hydroxyl-diacetate (73a) has also been reacted with SOCl₂-pyridine. The 3β-hydroxy- (81b) 5,6α-epoxy-9β-cholestanes have been prepared, and reacted with BF₃-etherate in benzene and/or ether. The major products have been shown to be ring A spiran compounds with some being formed via a ring B fragmentation reaction.

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Ngā upoko tukutuku/Māori subject headings
ANZSRC fields of research
Rights
Copyright C. N. Muir