Syntheses of Fused Ring Compounds Related to the Steroids and Dicyclic Sesquiterpenes

Philip, Robert (1946) Syntheses of Fused Ring Compounds Related to the Steroids and Dicyclic Sesquiterpenes. PhD thesis, University of Glasgow.

Abstract

PART I. An attempted synthesis of tetrahydro-beta-vetivone, shown by St. Pfau and Plattner to be (B), led to the preparation of a number of stereochemically pure cyclopentane derivatives related to this compound, and particularly to a stereochemically pure sample of 1-isopropyl-cyclopentane-3:4 bis (beta-butyric acid) (A). PART II. A new synthetic route to 9-methyl-l-decalone (C) by the use of a novel Reformatsky reaction between 2-methylcyclohexanone and methyl gamma-bromocrotonate is described. A ketone, believed to be l-keto-13-methyl-Delta11:12-dodecahydrophenanthrene (D) , has also been obtained. The constitution of a ketone (E) or (F), obtained by a "Stobbe condensation" between 2-methylcyclohexanone and diethyl succinate, followed by cyclisation, decarbethoxyla-tion, and hydrogenation, is discussed. (Diagram redacted) PART III. A projected steroid synthesis using 2-chloro-methylene-1:2:3:4-tetratiydronaphthalene (G) as an intermediate led to the syntheses of various hydrocoumarin derivatives (H).

• Item Type: Thesis (PhD)
• Qualification Level: Doctoral
• Keywords: Organic chemistry
• Date of Award: 1946
• Depositing User: Enlighten Team
• Unique ID: glathesis:1946-79666
• Copyright: Copyright of this thesis is held by the author.
• Date Deposited: 04 Mar 2020 15:43
• Last Modified: 04 Mar 2020 15:43
• URI: https://theses.gla.ac.uk/id/eprint/79666