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 leadi...

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Bibliographic Details
Main Author: Foucher, Vincent
Other Authors: Linclau, Bruno
Published: University of Southampton 2010
Subjects:
547.7
QD Chemistry
Online Access:https://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.538993
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spelling ndltd-bl.uk-oai-ethos.bl.uk-5389932018-09-05T03:28:02ZA novel, versatile D-BCD steroid construction strategy, illustrated by the total syntheses of estrone and desogestrelFoucher, VincentLinclau, Bruno2010Proposed 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 reaction547.7QD ChemistryUniversity of Southamptonhttps://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.538993https://eprints.soton.ac.uk/191321/Electronic Thesis or Dissertation
collection NDLTD
sources NDLTD
topic 547.7
QD Chemistry
spellingShingle 547.7
QD Chemistry
Foucher, Vincent
A novel, versatile D-BCD steroid construction strategy, illustrated by the total syntheses of estrone and desogestrel
description 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
author2 Linclau, Bruno
author_facet Linclau, Bruno
Foucher, Vincent
author Foucher, Vincent
author_sort Foucher, Vincent
title A novel, versatile D-BCD steroid construction strategy, illustrated by the total syntheses of estrone and desogestrel
title_short A novel, versatile D-BCD steroid construction strategy, illustrated by the total syntheses of estrone and desogestrel
title_full A novel, versatile D-BCD steroid construction strategy, illustrated by the total syntheses of estrone and desogestrel
title_fullStr A novel, versatile D-BCD steroid construction strategy, illustrated by the total syntheses of estrone and desogestrel
title_full_unstemmed A novel, versatile D-BCD steroid construction strategy, illustrated by the total syntheses of estrone and desogestrel
title_sort novel, versatile d-bcd steroid construction strategy, illustrated by the total syntheses of estrone and desogestrel
publisher University of Southampton
publishDate 2010
url https://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.538993
work_keys_str_mv AT fouchervincent anovelversatiledbcdsteroidconstructionstrategyillustratedbythetotalsynthesesofestroneanddesogestrel
AT fouchervincent novelversatiledbcdsteroidconstructionstrategyillustratedbythetotalsynthesesofestroneanddesogestrel
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