A novel scalable and stereospecific synthesis of 3α- and 3β-amino-5α-androstan-17-ones and 3α- and 3β-amino- 5α-pregnan-20-ones

James Hitchin, Niall Hamilton, Allan Jordan, Amanda J. Lyons, Donald Ogilvie

Research output: Contribution to journalArticlepeer-review

Abstract

A novel scalable stereoselective synthesis of 3α- and 3β-amino-5α-androstan-17-ones and 3α- and 3β-amino- 5α-pregnan-20-ones has been developed using phthalimide based Mitsunobu chemistry. In all four cases, the products were isolated as single diastereoisomers in high chemical yield and purity without the need for chromatography at any stage in their syntheses. © 2012 Elsevier Ltd. All rights reserved..
Original languageEnglish
Pages (from-to)2868-2872
Number of pages4
JournalTetrahedron Letters
Volume53
Issue number23
DOIs
Publication statusPublished - 6 Jun 2012

Keywords

  • Mitsunobu reaction
  • Phthalimide
  • Scalability
  • Stereoselectivity
  • Steroid

Research Beacons, Institutes and Platforms

  • Manchester Cancer Research Centre

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