Syntheses and biological evaluation of irciniastatin A and the C1-C2 alkyne analogue

Tsubasa Watanabe; Takamichi Imaizumi; Takumi Chinen; Yoko Nagumo; Masatoshi Shibuya; Takeo Usui; Naoki Kanoh; Yoshiharu Iwabuchi

doi:10.1021/ol1000389

Syntheses and biological evaluation of irciniastatin A and the C1-C2 alkyne analogue

Tsubasa Watanabe, Takamichi Imaizumi, Takumi Chinen, Yoko Nagumo, Masatoshi Shibuya, Takeo Usui, Naoki Kanoh, Yoshiharu Iwabuchi

PHA - Molecular Pharmaceutical Science

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

48 Citations (Scopus)

Abstract

"Chemical equation presented" Syntheses of both natural (+)- and unnatural (-)-irciniastatin A (aka psymberin) as well as a C1-C2 alkyne analogue of (+)-irciniastatin A have been achieved. The key features of the syntheses include a highly regioselective epoxide-opening reaction and a late-stage assembly of C1-C6, C8-C16, and C17-C25 fragments. (+)-Alkymberin retained a high level of cytotoxicity, whereas (-)-irciniastatin A showed almost no activity. These results suggest that (+)-alkymberin could be a useful enantio-differential probe for mode-of-action study.

Original language	English
Pages (from-to)	1040-1043
Number of pages	4
Journal	Organic letters
Volume	12
Issue number	5
DOIs	https://doi.org/10.1021/ol1000389
Publication status	Published - 2010 Mar 5

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "{"}Chemical equation presented{"} Syntheses of both natural (+)- and unnatural (-)-irciniastatin A (aka psymberin) as well as a C1-C2 alkyne analogue of (+)-irciniastatin A have been achieved. The key features of the syntheses include a highly regioselective epoxide-opening reaction and a late-stage assembly of C1-C6, C8-C16, and C17-C25 fragments. (+)-Alkymberin retained a high level of cytotoxicity, whereas (-)-irciniastatin A showed almost no activity. These results suggest that (+)-alkymberin could be a useful enantio-differential probe for mode-of-action study.",

author = "Tsubasa Watanabe and Takamichi Imaizumi and Takumi Chinen and Yoko Nagumo and Masatoshi Shibuya and Takeo Usui and Naoki Kanoh and Yoshiharu Iwabuchi",

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T1 - Syntheses and biological evaluation of irciniastatin A and the C1-C2 alkyne analogue

AU - Watanabe, Tsubasa

AU - Imaizumi, Takamichi

AU - Chinen, Takumi

AU - Nagumo, Yoko

AU - Shibuya, Masatoshi

AU - Usui, Takeo

AU - Kanoh, Naoki

AU - Iwabuchi, Yoshiharu

PY - 2010/3/5

Y1 - 2010/3/5

N2 - "Chemical equation presented" Syntheses of both natural (+)- and unnatural (-)-irciniastatin A (aka psymberin) as well as a C1-C2 alkyne analogue of (+)-irciniastatin A have been achieved. The key features of the syntheses include a highly regioselective epoxide-opening reaction and a late-stage assembly of C1-C6, C8-C16, and C17-C25 fragments. (+)-Alkymberin retained a high level of cytotoxicity, whereas (-)-irciniastatin A showed almost no activity. These results suggest that (+)-alkymberin could be a useful enantio-differential probe for mode-of-action study.

AB - "Chemical equation presented" Syntheses of both natural (+)- and unnatural (-)-irciniastatin A (aka psymberin) as well as a C1-C2 alkyne analogue of (+)-irciniastatin A have been achieved. The key features of the syntheses include a highly regioselective epoxide-opening reaction and a late-stage assembly of C1-C6, C8-C16, and C17-C25 fragments. (+)-Alkymberin retained a high level of cytotoxicity, whereas (-)-irciniastatin A showed almost no activity. These results suggest that (+)-alkymberin could be a useful enantio-differential probe for mode-of-action study.

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Syntheses and biological evaluation of irciniastatin A and the C1-C2 alkyne analogue

Abstract

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