Synthesis of a homostatine-containing renin inhibitor which incorporates a sulfonemethylene isostere at its N-terminus.

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A homostatine analogue, (2RS,4S,5S)N-isobutyl-5-amino-2-ethyl-4-hydroxy-7-methyloctanamide, was synthesized starting from natural statine. The modified Horner–Wadsworth–Emmons reaction of (4S,5R)-3-benzyloxycarbonyl-5-formyl-4-isobutyl-2,2-dimethyloxazolidine is a key reaction for the synthesis of a homostatine analogue. Stereoselective and stereospecific syntheses of a N-terminal precursor, N-[(2R)-3-hydroxy-2-(1-naphthylmethyl)propionyl]-L-norleucine t-butyl ester and a total synthesis of a highly active renin inhibitor, (2RS,4S,5S)-N-isobutyl-5-[[N-[(2S)-2-(1-naphthylmethyl)-3-(2-pyrimidinylsulfonyl)propionyl]-L-norleucyl]amino]-2-ethyl-4-hydroxy-7-methyloctanamide are described.
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