- A practical diastereoselective synthesis of (?)-bestatin
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Diastereoselective addition of nitromethane to Boc-D-Phe-H in the presence of sodium hydride in diethyl ether/hexane containing 15-crown-5 and subsequent N,O-protection with 2,2-dimethoxypropane gave trans-oxazolidine in a diastereomeric ratio of >16:1. T
- Shang, Suisheng,Willems, Andreas V.,Chauhan, Satendra S.
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- Asymmetric Nitroaldol Reaction. Synthesis of Taxotere Side Chain and (-)-Bestatin Using (1R)-8-Phenylmenthyl Glyoxylate
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The nitroaldol reaction of (1R)-8-phenylmenthyl glyoxylate (3b) with 1-nitro-1-phenylmethane (4) or with 1-nitro-2-phenylethane (13) led stereoselectively to adducts syn-2b and syn-12b, which were then transformed into the Taxotere side chain and (-)-best
- Kudyba, Iwona,Raczko, Jerzy,Jurczak, Janusz
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p. 2844 - 2850
(2007/10/03)
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- Application of acyl cyanophosphorane methodology to the synthesis of protease inhibitors: Poststatin, eurystatin, phebestin, probestin and bestatin
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Full details are given for the syntheses of the protease inhibitors, poststatin and eurystatin by the acyl cyanophosphorane coupling procedure used for the formation of α-keto amides. We have also extended this methodology to the syntheses of the related α-hydroxy amide natural products, phebestin, probestin and bestatin. The key step in the latter synthetic sequences involved diastereomeric selectivity in the reduction of the α-keto precursor to the corresponding α-hydroxy amide by the use of zinc borohydride.
- Wasserman, Harry H.,Petersen, Anders K.,Xia, Mingde
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p. 6771 - 6784
(2007/10/03)
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- Synthesis of (-)-bestatin and the Taxotere side-chain via nitroaldol reaction of (1R)-8-phenylmenthyl glyoxylate
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The nitroaldol reaction of (1R)-8-phenylmenthyl glyoxylate 6 with 1-nitro-2-phenylethane or with phenylnitromethane led stereoselectively to adducts 4 and 12, which where then transformed into (-)-bestatin hydrochloride and the Taxotere side-chain in over
- Kudyba, Iwona,Raczko, Jerzy,Jurczak, Janusz
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p. 8685 - 8687
(2007/10/03)
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- A new one-pot method for the synthesis of α-siloxyamides from aldehydes or ketones and its application to the synthesis of (-)-bestatin
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(equation presented) A new one-pot method for the synthesis of α-siloxyamides is described. The three substrates, H-C(CN)2O-SiMe2t-Bu, aldehydes or ketones, and primary or secondary amines, are simply mixed in one portion in acetonitrile or ether; the α-siloxyamides are obtained within short peroids in excellent yields in many cases. As a demonstration of our method, the synthesis of (-)-bestatin was carried out.
- Nemoto, Hisao,Ma, Rujian,Suzuki, Ichiro,Shibuya, Masayuki
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p. 4245 - 4247
(2007/10/03)
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- Novel synthesis of (-)-bestatin from L-aspartic acid
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Oxazoline-4-acetate derivative 3 that could be readily obtained from L-aspartic acid was subjected to highly stereoselective hydroxylation, and subsequent Mitsunobu inversion of the hydroxyl group led to (2S,3R)-3-amino-3-benzyl-2-hydroxybutanoic acid der
- Seki, Masahiko,Nakao, Kazuya
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p. 1304 - 1307
(2007/10/03)
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- A stereospecific synthesis of (-)-bestatin from L-malic acid
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A highly diastereospecific route to (-)-Bestatin from L-Malic Acid has been developed. This approach features a stereocontrolled alkylation of diethyl (S)-malate and proceeds through an oxazolidone via a Curtius Rearrangement.
- Norman,Morris
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p. 6803 - 6806
(2007/10/02)
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