Efficient construction of the kedarcidin chromophore ansamacrolide

Yasuhito Koyama; Martin J. Lear; Fumihiko Yoshimura; Isao Ohashi; Tomoko Mashimo; Masahiro Hirama

doi:10.1021/ol0477374

Efficient construction of the kedarcidin chromophore ansamacrolide

Yasuhito Koyama, Martin J. Lear, Fumihiko Yoshimura, Isao Ohashi, Tomoko Mashimo, Masahiro Hirama

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

34 Citations (Scopus)

Abstract

(Chemical Equation Presented) 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/CH ₂I₂ as a new entry to gem-disubstituted epoxides from ketones, both being applicable to 49-g scales.

Original language	English
Pages (from-to)	267-270
Number of pages	4
Journal	Organic letters
Volume	7
Issue number	2
DOIs	https://doi.org/10.1021/ol0477374
Publication status	Published - 2005 Jan 20
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol0477374

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abstract = "(Chemical Equation Presented) 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/CH 2I2 as a new entry to gem-disubstituted epoxides from ketones, both being applicable to 49-g scales.",

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AU - Koyama, Yasuhito

AU - Lear, Martin J.

AU - Yoshimura, Fumihiko

AU - Ohashi, Isao

AU - Mashimo, Tomoko

AU - Hirama, Masahiro

PY - 2005/1/20

Y1 - 2005/1/20

N2 - (Chemical Equation Presented) 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/CH 2I2 as a new entry to gem-disubstituted epoxides from ketones, both being applicable to 49-g scales.

AB - (Chemical Equation Presented) 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/CH 2I2 as a new entry to gem-disubstituted epoxides from ketones, both being applicable to 49-g scales.

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Efficient construction of the kedarcidin chromophore ansamacrolide

Abstract

ASJC Scopus subject areas

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