Total synthesis of a protected aglycon of the kedarcidin chromophore

Kouki Ogawa; Yasuhito Koyama; Isao Ohashi; Itaru Sato; Masahiro Hirama

doi:10.1002/anie.200805518

Total synthesis of a protected aglycon of the kedarcidin chromophore

Kouki Ogawa, Yasuhito Koyama, Isao Ohashi, Itaru Sato, Masahiro Hirama

SCI - Research and Analytical Center for Giant Molecules

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

26 Citations (Scopus)

Abstract

(Chemical Equation Presented) Strong support for the recently proposed structure of the kedarcidin chromophore has been obtained through the convergent synthesis of the aglycon. The key features of the synthesis are an efficient assembly of the four fragments, a novel strategy involving an alkynyl epoxide, a cerium amide promoted nine-membered diyne ring cyclization, and a SmI ₂-mediated reductive 1,2-elimination. TBS=tert-butyldimethylsilyl, MOM=methoxymethyl.

Original language	English
Pages (from-to)	1110-1113
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	48
Issue number	6
DOIs	https://doi.org/10.1002/anie.200805518
Publication status	Published - 2009 Jan 26

Keywords

Antitumor agents
Chromophores
Cyclization
Enediynes
Total synthesis

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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10.1002/anie.200805518

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abstract = "(Chemical Equation Presented) Strong support for the recently proposed structure of the kedarcidin chromophore has been obtained through the convergent synthesis of the aglycon. The key features of the synthesis are an efficient assembly of the four fragments, a novel strategy involving an alkynyl epoxide, a cerium amide promoted nine-membered diyne ring cyclization, and a SmI 2-mediated reductive 1,2-elimination. TBS=tert-butyldimethylsilyl, MOM=methoxymethyl.",

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T1 - Total synthesis of a protected aglycon of the kedarcidin chromophore

AU - Ogawa, Kouki

AU - Koyama, Yasuhito

AU - Ohashi, Isao

AU - Sato, Itaru

AU - Hirama, Masahiro

PY - 2009/1/26

Y1 - 2009/1/26

N2 - (Chemical Equation Presented) Strong support for the recently proposed structure of the kedarcidin chromophore has been obtained through the convergent synthesis of the aglycon. The key features of the synthesis are an efficient assembly of the four fragments, a novel strategy involving an alkynyl epoxide, a cerium amide promoted nine-membered diyne ring cyclization, and a SmI 2-mediated reductive 1,2-elimination. TBS=tert-butyldimethylsilyl, MOM=methoxymethyl.

AB - (Chemical Equation Presented) Strong support for the recently proposed structure of the kedarcidin chromophore has been obtained through the convergent synthesis of the aglycon. The key features of the synthesis are an efficient assembly of the four fragments, a novel strategy involving an alkynyl epoxide, a cerium amide promoted nine-membered diyne ring cyclization, and a SmI 2-mediated reductive 1,2-elimination. TBS=tert-butyldimethylsilyl, MOM=methoxymethyl.

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KW - Chromophores

KW - Cyclization

KW - Enediynes

KW - Total synthesis

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Total synthesis of a protected aglycon of the kedarcidin chromophore

Abstract

Keywords

ASJC Scopus subject areas

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