Novel Synthesis of a Dihydroxyethylene Isostere of Renin Inhibitors

Shugo ATSUUMI; Chinatsu IKEURA; Teruki HONMA; Hajime MORISHIMA

doi:10.1248/cpb.42.2164

Shugo ATSUUMI, Chinatsu IKEURA, Teruki HONMA, Hajime MORISHIMA

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Keywords: renin inhibitor, dihydroxyethylene isostere, stereospecific synthesis, iodo-cyclocarbamation, (2S, 3R, 4S)-4-amino-5-cyclohexyl-1-morpholino-2, 3-pentanediol

JOURNAL FREE ACCESS

1994 Volume 42 Issue 10 Pages 2164-2166

DOI https://doi.org/10.1248/cpb.42.2164

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Abstract

A dihydroxyethylene isostere, (2S, 3R, 4S)-4-amino-5-cyclohexyl-1-morpholino-2, 3-pentanediol (ACMP, 1), which is a component of non-peptidic, orally active, low-molecular-weight renin inhibitors, was synthesized stereospecifically starting from 3-cyclohexyl-L-alanine via iodo-cyclocarbamation as the key reaction.

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