Pot Economy in the Total Synthesis of Estradiol Methyl Ether by Using an Organocatalyst

Yujiro Hayashi, Seitaro Koshino, Kanna Ojima, Eunsang Kwon

Research output: Contribution to journalArticlepeer-review

26 Citations (Scopus)

Abstract

Enantioselective total synthesis of estradiol methyl ether has been accomplished in a pot-economical manner using five reaction vessels and four purifications. The key reaction is a diphenylprolinol silyl ether mediated domino Michael/aldol reaction to afford bicyclo[4.3.0]nonane derivatives, containing the A, C, and D rings of steroids, as a single isomer with excellent enantioselectivity. Six reactions such as oxidation, hydrogenation, formation of acid chloride, Friedel–Crafts reaction, deprotection, and reduction can be carried out in the last one-pot sequence.

Original languageEnglish
Pages (from-to)11812-11815
Number of pages4
JournalAngewandte Chemie - International Edition
Volume56
Issue number39
DOIs
Publication statusPublished - 2017 Sep 18

Keywords

  • asymmetric synthesis
  • domino reactions
  • organocatalysis
  • steroids
  • total synthesis

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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