• Applied Chemistry for Engineering
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• v.25 no.5
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• pp.437-446
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• 2014

The dihydroxylation reaction of allylic amines is a facile and useful synthetic method to obtain amino diol structures that are widely found in lots of biologically important natural products. This review will focus on the recent methods of both substrate-controlled and ligand-controlled dihydroxylation reactions of acyclic allylic amines. In addition, several applications of the diastereoselective dihydroxylation methods to asymmetric syntheses of natural products are presented.

• Bulletin of the Korean Chemical Society
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• v.25 no.11
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• pp.1671-1675
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• 2004

A simple method for simultaneous recovery and reuse of $OsO_4$ and alkaloid ligand in the asymmetric dihydroxylation of olefins has been developed by using macroporous alkaloid resins bearing residual vinyl groups.

• Archives of Pharmacal Research
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• v.20 no.2
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• pp.144-147
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• 1997

A novel synthetic method was developed for 3-hydroxyhomoisoflavanone. Treatment of aryllithium 14 to aldehyde 13 which was obtained from dihydroxylation of 10, followed by cycloetherification to give 3-hydroxyhomoisoflavanones.

• Bulletin of the Korean Chemical Society
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• v.30 no.5
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• pp.1147-1151
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• 2009

The synthetic route of novel 3′-C-methyl carbodine analogue is described. The construction of tertiary alcohol at 3′- position of carbodine analogues was successfully made via sequential [3,3]-sigmatropic rearrangement, ring-closing metathesis (RCM) and stereoselective dihydroxylation reactions starting from ethyl glycolate.

• Applied Chemistry for Engineering
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• v.31 no.2
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• pp.187-192
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• 2020

(2S,3R)-3-hydroxyhomoserine lactone (HSL) has been used as a key intermediate for the synthesis of various biologically active compounds. In this study, we demonstrated an efficient synthesis of HSL via anti selective dihydroxylation of a protected vinyl glycine analog with an oxabicyclo[2.2.2]octyl orthoester (OBO) ester group. Because the acyclic conformation of the substrate was efficiently controlled by the bulky OBO ester group, a diastereoselectivity of > 10 : 1 was obtained in the dihydroxylation reaction without the use of a chiral reagent. By using this result, the target compound 1 can be obtained from commercially available N-Cbz-L-serine 2 in seven steps with an overall yeid of 34%. This result could be applied to the stereoselective synthesis of biologically active molecules containing a vicinal amino diol moiety.

• Bulletin of the Korean Chemical Society
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• v.26 no.11
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• pp.1839-1842
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• 2005

• Bulletin of the Korean Chemical Society
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• v.23 no.9
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• pp.1197-1244
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• 2002

• Bulletin of the Korean Chemical Society
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• v.32 no.spc8
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• pp.2949-2954
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• 2011

This paper describes a concise and efficient synthetic route for the biologically interesting pyranoxanthones, dihydropyranoxanthones, and their derivatives. The key strategies involve pyranyl ring formation, methylation, catalytic hydrogenation, and catalytic dihydroxylation starting from 1,3-dihydroxyxanthen-9-one.

• Bulletin of the Korean Chemical Society
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• v.23 no.3
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• pp.507-508
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• 2002

• Applied Chemistry for Engineering
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• v.25 no.4
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• pp.392-395
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• 2014

(2S,3S,4S)-3,4-Dihydroxyglutamic acid (DHGA), a biologically active ${\alpha},{\beta}$-dihydroxy-${\gamma}$-amino acid, was efficiently synthesized from a readily available D-serine derivative in 30% overall yield over 11 steps. The key stereoselective $OsO_4$-catalyzed dihydroxylation reaction controlled by an N-diphenylmethylene group on the amino group of ${\gamma}$-amino-${\alpha},{\beta}$-unsaturated (Z)-ester successfully introduced the diol moiety of the intermediate 5a in 86% with more than 10 : 1 diastereomeric ration. Then it was in turn successfully converted to the desired target compound, (2S,3S,4S)-3,4-DHGA, via simple oxidation and hydrolysis in a highly stereoselective manner and a higher yield than the previous syntheses. This result strongly supports that our synthetic methodology of stereoselective $OsO_4$-catalyzed dihydroxylation should be useful in stereoselctive synthesis of various bioactive compounds with an amino diol moiety.