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 language | English |
|---|---|
| Pages (from-to) | 768-778 |
| Number of pages | 11 |
| Journal | Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry |
| Volume | 71 |
| Issue number | 8 |
| DOIs | |
| Publication status | Published - 2013 Dec 16 |
Keywords
- Angiogenesis inhibitor
- Cortistatin
- Isoquinoline unit
- Knoevenagel/electrocyclic reactions
- Radical cyclization
- Steroidal alkaloid
- Total synthesis
ASJC Scopus subject areas
- Organic Chemistry