Total synthesis of cortistatin A and J

Shuji Yamashita, Masahiro Hirama

Research output: Contribution to journalReview articlepeer-review

2 Citations (Scopus)

Abstract

Cortistatins, isolated from Cortisium simplex in 2006, exhibit potent inhibition against the proliferation of human umbilical vein endothelial cells (HUVECs). This paper describes the details of our total synthesis of cortistatins A and J. The key features of our strategy include (1) an efficient Knoevenagel/electrocyclic reactions to couple the diketone and the CD-ring fragment, (2) a chemoselective radical cyclization to construct the oxabicyclo[3.2.1]octane system, (3) a highly stereocontrolled installation of the isoquinoline unit, and (4) a late-stage functionalization of the A-ring.

Original languageEnglish
Pages (from-to)768-778
Number of pages11
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume71
Issue number8
DOIs
Publication statusPublished - 2013 Dec 16

Keywords

  • Angiogenesis inhibitor
  • Cortistatin
  • Isoquinoline unit
  • Knoevenagel/electrocyclic reactions
  • Radical cyclization
  • Steroidal alkaloid
  • Total synthesis

ASJC Scopus subject areas

  • Organic Chemistry

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