A novel approach in drug discovery: Synthesis of estrone - Talaromycin natural product hybrids

Lutz F. Tietze, Gyula Schneider, János Wölfling, Anja Fecher, Thomas Nöbel, Sönke Petersen, Ingrid Schuberth, Christian Wulff

Research output: Contribution to journalArticle

54 Citations (Scopus)

Abstract

Hetero-Diels - Alder reaction of the steroidal exocyclic enol ethers 14 and 15, obtained from the secoestrones 8 and 9 by reduction, iodoetherification, and elimination, with ethyl O-benzoyldiformylacetate (16) leads to the spiroacetals 17 and 18 as a mixture of four diastereomers. Reduction of the major diastereomers 17 a and 18a with DIBAH and subsequent hydrogenation yields the novel natural product hybrids 21, 23, 24, and 25, which possess the structural features of the steroid estrone (7) and the mycotoxin talaromycin 6.

Original languageEnglish
Pages (from-to)3755-3760
Number of pages6
JournalChemistry - A European Journal
Volume6
Issue number20
DOIs
Publication statusPublished - Oct 16 2000

Keywords

  • Anticancer agents
  • Combinatorial chemistry
  • Cycloadditions
  • Spiro compounds
  • Steroids
  • Talaromycin

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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