Art

J-GLOBAL ID：200902273781213860   Reference number：08A0142204

Stereoselective Construction of Tetra-Substituted Tetrahydrofuran Compounds from Benzylic Hemiacetal in the Presence of H₂ and a Pd Catalyst: Stereoselective Synthesis of a Stereoisomer of (-)-Virgatusin and Its Antimicrobiological Activity

H₂およびPd触媒の存在下におけるベンジル型ヘミアセタールからの四置換テトラヒドロフラン化合物の立体選択的構築: (-)-ビルガツシン立体異性体の立体選択的合成およびその抗微生物活性

Author (7)： NAKATO Tomofumi (Fac. of Agriculture, Ehime Univ.) ,  TAGO Ryosuke (Fac. of Agriculture, Ehime Univ.) ,  AKIYAMA Koichi (Integrated Center for Sciences, Tarumi Station, Ehime Univ.) ,  MARUYAMA Masafumi (Fac. of Agriculture, Ehime Univ.) ,  SUGAHARA Takuya (Fac. of Agriculture, Ehime Univ.) ,  KISHIDA Taro (Fac. of Agriculture, Ehime Univ.) ,  YAMAUCHI Satoshi (Fac. of Agriculture, Ehime Univ.)
Material： Bioscience, Biotechnology, and Biochemistry  (Bioscience Biotechnology & Biochemistry)
Volume： 72  Issue： 1  Page： 197-203 (J-STAGE)  Publication year： 2008 
JST Material Number： G0021A  ISSN： 0916-8451  CODEN： BBBIEJ  Document type： Article
Article type： 原著論文  Country of issue： Japan (JPN)  Language： ENGLISH (EN)

Thesaurus term： palladium catalyst ,...

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JST classification (1)： Furans  (CF07072V)

Substance index (8)： Tetrahydrofuran ,  (2S)-2α-(1,3-Benzodioxole-5-yl)-3α,4β-bis(pivaloyloxymethyl)-5α-(3,4-dimethoxyphenyl)tetrahydrofuran ,  (2R)-2β-(1,3-Benzodioxole-5-yl)-3β,4β-bis(pivaloyloxymethyl)-5α-(3,4-dimethoxyphenyl)tetrahydrofuran ,  (2R)-2β-(1,3-Benzodioxole-5-yl)-3β,4β-bis(hydroxymethyl)-5α-(3,4-dimethoxyphenyl)tetrahydrofuran ,  (2S)-2α-(1,3-Benzodioxole-5-yl)-3α,4α-bis(hydroxymethyl)-5β-(3,4-dimethoxyphenyl)tetrahydrofuran ,  (2R)-2β-(1,3-Benzodioxole-5-yl)-3α,4α-bis(hydroxymethyl)-5β-(3,4-dimethoxyphenyl)tetrahydrofuran ,  (2S)-2α-(1,3-Benzodioxole-5-yl)-3β,4β-bis(hydroxymethyl)-5α-(3,4-dimethoxyphenyl)tetrahydrofuran ,  (2R)-2β-(1,3-Benzodioxole-5-yl)-5β-(3,4-dimethoxyphenyl)tetrahydrofuran-3β,4α-dimethanol

Reference (14)：

• 1) Czernecki, S., and Ville, G., C-glycosides 7. Stereospecific C-glycosylation of aromatic and heterocyclic rings. J. Org. Chem., 54, 610–612 (1989).
• 2) Shing, T. K. M., and Gillhouley, J. G., Enantiospecific synthesis of (+)-altholactone and its three stereoisomers. Tetrahedron, 50, 8685–8698 (1994).
• 3) Nishiyama, Y., Tujino, T., Yamano, T., Hayashishita, M., and Itoh, K., Stereoselective synthesis of trans-2,5-disubstituted tetrahydrofuran via the Lewis acid mediated reduction of cyclic hemiketals with triphenylsilane. Chem. Lett., 165–166 (1997).
• 4) Shionoya, M., and Tanaka, K., Synthetic incorporation of metal complexes into nuleic acids and peptides directed toward functionalized molecules. Bull. Chem. Soc. Japan, 73, 1945–1954 (2000).
• 5) Schmitt, A., and Reißig, H.-U., On the stereoselectivity of γ-lactol substitutions with allyl- and propargylsilanes–synthesis of disubstituted tetrahydrofuran derivatives. Eur. J. Org. Chem., 3893–3901 (2000).

Terms in the title (11)： H2 ,  Pd触媒 ,  ベンジル ,  ヘミアセタール ,  置換 ,  テトラヒドロフラン ,  立体 ,  構築 ,  立体異性体 ,  立体選択的合成 ,  抗微生物活性