Efficient Construction of the Kedarcidin Chromophore Ansamacrolide | Zendy

Yasuhito Koyama | Zendy; Martin J. Lear | Zendy; Fumihiko Yoshimura | Zendy; Isao Ōhashi | Zendy; Tomoko Mashimo | Zendy; Masahiro Hirama | Zendy

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Efficient Construction of the Kedarcidin Chromophore Ansamacrolide

Author(s) -

Yasuhito Koyama,

Martin J. Lear,

Fumihiko Yoshimura,

Isao Ōhashi,

Tomoko Mashimo,

Masahiro Hirama

Publication year - 2004

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/ol0477374

Subject(s) - sonogashira coupling , chromophore , chemistry , cyclopentene , combinatorial chemistry , coupling (piping) , catalysis , stereochemistry , organic chemistry , palladium , mechanical engineering , engineering

[Structure: see text] The streamlined assembly of the ansamacrolide framework of the kedarcidin chromophore via an efficient atropselective Sonogashira coupling step is described. To this end, two newly improved practical syntheses of the cyclopentene and diyne fragments have been developed, which feature 0.2 mol % catalytic loadings for an RCM step and i-PrMgCl/CH2I2 as a new entry to gem-disubstituted epoxides from ketones, both being applicable to 49-g scales.

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