Total synthesis of cortistatin A and J

Shuji Yamashita; Masahiro Hirama

doi:10.5059/yukigoseikyokaishi.71.768

Total synthesis of cortistatin A and J

Shuji Yamashita, Masahiro Hirama

SCI - Chemistry

Research output: Contribution to journal › Review article › peer-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 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	https://doi.org/10.5059/yukigoseikyokaishi.71.768
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

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title = "Total synthesis of cortistatin A and J",

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.",

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author = "Shuji Yamashita and Masahiro Hirama",

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doi = "10.5059/yukigoseikyokaishi.71.768",

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AU - Yamashita, Shuji

AU - Hirama, Masahiro

PY - 2013/12/16

Y1 - 2013/12/16

N2 - 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.

AB - 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.

KW - Angiogenesis inhibitor

KW - Cortistatin

KW - Isoquinoline unit

KW - Knoevenagel/electrocyclic reactions

KW - Radical cyclization

KW - Steroidal alkaloid

KW - Total synthesis

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JO - Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry

JF - Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry

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Total synthesis of cortistatin A and J

Abstract

Keywords

ASJC Scopus subject areas

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