Stereoselective Synthesis of Optically Active 4-Ethyl-3, 5-dihydroxy-2-methylpentyl Derivatives. A Basic Building Block with Three Contiguous Chiral Centers of Polyether Antibiotics

Kiyoshi HORITA; Kazuhiro TANAKA; Osamu YONEMITSU

doi:10.1248/cpb.41.2044

Kiyoshi HORITA, Kazuhiro TANAKA, Osamu YONEMITSU

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Keywords: polyether antibiotic, stereoselective synthesis, chiral synthon, asymmetric epoxidation, organocopper reagent, protecting group

JOURNAL FREE ACCESS

1993 Volume 41 Issue 11 Pages 2044-2046

DOI https://doi.org/10.1248/cpb.41.2044

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Abstract

Optically active 4-ethyl-3, 5-dihydroxy-2-methylpentyl derivatives, the iodide (4), phenyl sulfone (5), and phenyl sulfoxide (6), which are chiral synthons for an essential structural unit of polyether antibiotics, were stereoselectively synthesized starting from commercially available methyl (2S)-3-hydroxy-2-methylpropionate (7) in good overall yield (33% for 18 steps).

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