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A novel, versatile D-BCD steroid construction strategy, illustrated by the total syntheses of estrone and desogestrel

A novel, versatile D-BCD steroid construction strategy, illustrated by the total syntheses of estrone and desogestrel
A novel, versatile D-BCD steroid construction strategy, illustrated by the total syntheses of estrone and desogestrel
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
Foucher, Vincent
5c33fbe0-3468-4f2f-938a-4349aaabe817
Foucher, Vincent
5c33fbe0-3468-4f2f-938a-4349aaabe817
Linclau, Bruno
19b9cacd-b8e8-4c65-af36-6352cade84ba

Foucher, Vincent (2010) A novel, versatile D-BCD steroid construction strategy, illustrated by the total syntheses of estrone and desogestrel. University of Southampton, Chemistry, Doctoral Thesis, 300pp.

Record type: Thesis (Doctoral)

Abstract

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

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Published date: 27 August 2010
Organisations: University of Southampton

Identifiers

Local EPrints ID: 191321
URI: http://eprints.soton.ac.uk/id/eprint/191321
PURE UUID: 3345ae86-295b-46d8-a317-975689636596
ORCID for Bruno Linclau: ORCID iD orcid.org/0000-0001-8762-0170

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Date deposited: 20 Jun 2011 12:25
Last modified: 30 Jan 2020 01:30

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