Total synthesis of cortistatins A and J

Shuji Yamashita; Kentaro Iso; Kazuki Kitajima; Masafumi Himuro; Masahiro Hirama

doi:10.1021/jo2002616

Total synthesis of cortistatins A and J

Shuji Yamashita, Kentaro Iso, Kazuki Kitajima, Masafumi Himuro, Masahiro Hirama

SCI - Chemistry

Research output: Contribution to journal › Article › peer-review

68 Citations (Scopus)

Abstract

This paper describes the details of our synthetic studies on the marine steroidal alkaloids cortistatins A and J. The key features of our strategy include (i) an efficient Knoevenagel/electrocyclic strategy to couple the diketone and the CD-ring fragment, (ii) a chemoselective radical cyclization to construct the oxabicyclo[3.2.1]octene B-ring system, (iii) a highly stereocontrolled installation of the isoquinoline unit, and (iv) a late-stage functionalization of the A-ring.

Original language	English
Pages (from-to)	2408-2425
Number of pages	18
Journal	Journal of Organic Chemistry
Volume	76
Issue number	8
DOIs	https://doi.org/10.1021/jo2002616
Publication status	Published - 2011 Apr 15

ASJC Scopus subject areas

Organic Chemistry

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This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1021/jo2002616

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AU - Yamashita, Shuji

AU - Iso, Kentaro

AU - Kitajima, Kazuki

AU - Himuro, Masafumi

AU - Hirama, Masahiro

PY - 2011/4/15

Y1 - 2011/4/15

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AB - This paper describes the details of our synthetic studies on the marine steroidal alkaloids cortistatins A and J. The key features of our strategy include (i) an efficient Knoevenagel/electrocyclic strategy to couple the diketone and the CD-ring fragment, (ii) a chemoselective radical cyclization to construct the oxabicyclo[3.2.1]octene B-ring system, (iii) a highly stereocontrolled installation of the isoquinoline unit, and (iv) a late-stage functionalization of the A-ring.

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Total synthesis of cortistatins A and J

Abstract

ASJC Scopus subject areas

UN SDGs

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