Total Synthesis of a Protected Aglycon of the Kedarcidin Chromophore

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 promote...

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Bibliographic Details
Published in:Angewandte Chemie (International ed.) 2009-01, Vol.48 (6), p.1110-1113
Main Authors: Ogawa, Kouki, Koyama, Yasuhito, Ohashi, Isao, Sato, Itaru, Hirama, Masahiro
Format: Article
Language:English
Subjects:
Antibiotics, Antineoplastic - chemical synthesis
Antibiotics, Antineoplastic - chemistry
antitumor agents
chromophores
Cyclization
Cycloparaffins - chemical synthesis
Cycloparaffins - chemistry
enediynes
Enediynes - chemical synthesis
Enediynes - chemistry
Magnetic Resonance Spectroscopy
Naphthalenes - chemical synthesis
Naphthalenes - chemistry
total synthesis
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Summary: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 SmI2‐mediated reductive 1,2‐elimination. TBS=tert‐butyldimethylsilyl, MOM=methoxymethyl.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200805518