Efficient and stereoselective installation of isoquinoline: formal total synthesis of cortistatin A

Shuji Yamashita, Kazuki Kitajima, Kentaro Iso, Masahiro Hirama

Research output: Contribution to journalArticlepeer-review

36 Citations (Scopus)

Abstract

The highly stereoselective attachment of isoquinoline onto the steroidal framework of cortistatin A has been achieved. Our strategy features a Ce-mediated nucleophilic addition of an isoquinoline unit to the sterically congested ketone followed by formation of the phenyl thiocarbamate, and subsequent stereoselective radical reduction. The new method results in a formal total synthesis of cortistatin A.

Original languageEnglish
Pages (from-to)3277-3279
Number of pages3
JournalTetrahedron Letters
Volume50
Issue number26
DOIs
Publication statusPublished - 2009 Jul 1

Keywords

  • Cortistatin A
  • Isoquinoline
  • Marine natural product
  • Total synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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