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Efficient construction of the kedarcidin chromophore ansamacrolide
Yasuhito Koyama1, Martin J Lear, Fumihiko Yoshimura
1Department of Chemistry, Graduate School of Science, Tohoku University, COE, Sendai 980-8578, Japan.
Organic Letters
|January 14, 2005
Abstract:
[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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