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University of Southampton
A novel, versatile D-BCD steroid construction strategy, illustrated by the total syntheses of estrone and desogestrel
Abstract
dc:description.abstractProposed 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
Degree
thesis:*- Name dc:type.qualificationname
- Ph.D.
- Level dc:type.qualificationlevel
- doctoral
- Grantor dc:publisher.institution
- University of Southampton
- Year dc:date.issued
- 2010
Author and committee
dc:creator, dc:contributor.*- Author dc:creator
-
- Foucher, Vincent
- Advisor dc:contributor.advisor
-
- Linclau, Bruno