Use this URL to cite or link to this record in EThOS:
Title: A novel, versatile D-BCD steroid construction strategy, illustrated by the total syntheses of estrone and desogestrel
Author: Foucher, Vincent
ISNI:       0000 0004 2707 8705
Awarding Body: University of Southampton
Current Institution: University of Southampton
Date of Award: 2010
Availability of Full Text:
Access from EThOS:
Access from Institution:
Proposed are the total syntheses of the steroids desogestrel and estrone, utilizing a 1,4 addition/alkylation process to install the correct stereochemistry at C8, C13 and C14 in a single-pot operation. The racemic total synthesis of desogestrel includes a successful domino anionic cyclisation leading to the formation of the steroid C and B rings in a single operation with complete stereocontrol at C9. The -keto phosphonates obtained were subsequently subjected to A-ring annelation via a multistep one-pot process. The enantioselective synthesis as well as the racemic total synthesis of estrone include a sequential C and B-ring formation through ring closing metathesis and intramolecular Heck reaction
Supervisor: Linclau, Bruno Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available
Keywords: QD Chemistry