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Paper | Regular issue | Vol 65, No. 11, 2005, pp.2657-2665
Published online, 2nd September, 2005
DOI: 10.3987/COM-05-10500
Asymmetric Synthesis of (2R,3R,4R)-3-Hydroxy-4-methylproline via Chromium(II) Chloride-mediated Coupling Reactions of (S)-Garner Aldehyde with Crotyl Bromide

Haruko Inaba, Yukiko Hiraiwa, Satoshi Yoshida, Mina Tamura, Asako Kuroda, Aki Ogawa, Yutaka Aoyagi, Akihiro Ohta, and Koichi Takeya*

*School of Pharmacy, Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan

Abstract

Efficient synthesis of (2R,4R,4R)-3-hydroxy-4-methylproline (1a), which is an antipode of the component of potent antifungal echinocandins, from (S)-Garner aldehyde (2a) has been established. The key step is chromium(II) chloride-mediated coupling reactions with crotyl bromide giving homoallyl alcohols (4a) and (4a’) in a ratio of 83:17.