[KSCI] Korea Science Citation Index Service

Facial Synthesis of Versatile Chiral Norbornenes as Leukotriene D4 Antagonists from D-glucose

Lim, Yoong-Ho (Department of Applied Chemistry, Dongduk Women's University)
Koh, Dong-Soo (Bio/Molecular Informatics Center, Department of Applied Biology and Chemistry, Konkuk University)

Publication Information

Journal of Applied Biological Chemistry / v.48, no.2, 2005 , pp. 97-100 More about this Journal

Abstract

Chiral dienophile 5 was synthesized from D-glucose by consecutive diisopropylidenation, partial deprotection, diol cleavage, and Wittig reactions. Under thermal conditions, asymmetric Diels-Alder reaction between chiral dienophile and cyclopentadiene gave four possible chiral norbornenes stereoisomers whose absolute configurations were determined through CADD and NMR.

Keywords

Asymmetric reaction; Chiral Dienophiles; Diels-Alder reaction; Stereochemistry;

Citations & Related Records

Reference

1	Diastereoselectivity of a [3+2] annulation. On the question of a dipole effect on a stereoselectivity of olefin addition / [ Trost, B.M.;Lynch, J.;Renaut, P. ] / Tetrahedron Lett. DOI
2	Stereocontrol in Diels-Alder cycloaddition to unsaturated sugars: Reactivities of cis dienophiles with cyclopentadiene / [ Horton, D.;Koh, D.;Takagi, Y. ] / Carbohydr. Res. DOI
3	Total synthesis of Griseolic acid derivatives from D-glucose / [ Tulshian, D.;Doll, R.;Stansberry, M.F. ] / J. Org. Chem. DOI
4	Enantioselective synthesis of S-1452, an orally active potent thromboxane A2 receptor antagonist / [ Ohitani, E.;Matsuura, T.;Watanabe, F.;Narisada, M. ] / J. Org. Chem. DOI
5	A C-Glycoside route to leukotrienes / [ Rokach, J.;Lau, C.K.;Zambony, R.;Guindon, Y. ] / Tetrahedron Lett.
6	Regio- and stereoselective ring openings of 3-aza-2-oxabicyclo[2.2.1]hept-5-ene systems with copper catalyst-modified grignard reagents: Application to the synthesis of an inhibitor of 5-lipoxygenase / [ Surman, M.D.;Mulvihill, M.J.;Miller, M.J. ] / J. Org. Chem. DOI
7	Rapid chromatographic technique for preparative separation with moderate resolution / [ Still, W.C.;Kahn, M.;Mitr, A. ] / J. Org. Chem. DOI
8	Methods in carbohydrate chemistry, vol. VI / [ Stevene, J.D. ] /
9	In Methods in carbohydrate chemistry, vol. II / [ Schmodt, O.T. ] /
10	General procedure for a one-pot oxidative cleavage/Wittig reaction of glycols / [ Dunlap, N.K.;Mergo, W.;Jones, J.M.;Carrick, D.A. ] / Tetrahedron Lett. DOI
11	Anti-allergic activity of a disaccharide isolated from Sanguisorba officinalis / [ Park, K.H.;Koh, D.;Park, J.;Kim, K.;Lim, Y. ] / Phytotherapy Research DOI
12	Synthesis and biological activities of leukotriene D4 antagonists predicted from quantitatively structure-activity relationship calculation / [ Koh, D.;Park, K.H.;Lim, Y. ] / Agric. Chem. Biotechnol.
13	Resveratrol derivatives showing the leukotriene D4 antagonism / [ Koh, D.;Park, K.H.;Lee, H.;Jung, J.;Lim, Y. ] / Agric. Chem. Biotechnol.
14	Anti-allergic and anti-asthmatic activity of Helioscopinin-A, a polyphenol compound, isolated from Euphorbia helioscopia / [ Koh, D.;Park, K.H.;Lee, S.;Jung, I.;Kim, K.;M.;Lee, C.;Kim, K.;Lim, Y. ] / J Mocrobiol. Biotechnol. DOI
15	Anti-allergic compound with Leukotriene D4 Antagonism isolated from Puerariae radix / [ Koh, D.;Park, K.H.;Lim, Y. ] / J. Korean Soc. Agric. Chem. Biotechnol.
16	Quantitatively Structure-activity Relationships to Develop Anti-asrhmatic Drugs / [ Koh, D.;Park, K.H.;Lee, H.;Jung, J.;Cho, S.K.;Lim, Y. ] / Agric. Chem. Biotechnol.
17	Effect of Saikosaponin-A, a triterpenoid glycoside, isolated from Bupueurum falcatum on experimental allergic asthma / [ Park, K.H.;Park, J.;Koh, D.;Lim, Y. ] / Phytotheraphy Research DOI
18	Stereocontrol in Diels-Alder cycloaddition to unsaturated sugars: Reactivities of acyclic 7-carbon trans dienophiles derived from aldopentoses / [ Horton, D.;Koh, D. ] / Carbohydr. Res. DOI