Art

J-GLOBAL ID：200902285013787405   Reference number：03A0782009

Systematic Strategy for the Synthesis of Cyanobacterin and Its Stereoisomers. 2. Asymmetric Total Synthesis of the 2- and 3-Epimers of Dechloro-cyanobacterin

シアノバクテリンおよびその立体異性体の合成の系統的戦略 2. 脱クロロ-シアノバクテリンの2-および3-エピマの非対称全合成

Author (3)： HAGA Y (Ehime Univ., Matsuyama, JPN) ,  OKAZAKI M (Ehime Univ., Matsuyama, JPN) ,  SHUTO Y (Ehime Univ., Matsuyama, JPN)
Material： Bioscience, Biotechnology, and Biochemistry  (Bioscience Biotechnology & Biochemistry)
Volume： 67  Issue： 10  Page： 2215-2223  Publication year： Oct. 23, 2003 
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： *bioactive factor ,...

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JST classification (2)： Other natural substances of biological origin  (CF10090R) ,  Microorganism biochemistry  (EG03020N)

Substance index (8)： Cyanobacterin ,  (R)-1-Hydroxy-2-(1,3-benzodioxole-5-ylmethyl)-4-methyl-3-pentanone ,  (4S)-3-[3-(1,3-Benzodioxole-5-yl)propionyl]-4-benzyloxazolidine-2-one ,  (S)-1-Hydroxy-2-(1,3-benzodioxole-5-ylmethyl)-4-methyl-3-pentanone ,  (3R,4R)-1-(4-Methoxyphenyl)-3-isopropyl-4-(1,3-benzodioxole-5-ylmethyl)-5-hydroxy-1-pentyne-3-ol ,  (3S,4S)-1-(4-Methoxyphenyl)-3-isopropyl-4-(1,3-benzodioxole-5-ylmethyl)-5-hydroxy-1-pentyne-3-ol ,  (3S)-3β-(1,3-Benzodioxole-5-ylmethyl)-4β-hydroxy-4-isopropyl-5-[(Z)-4-methoxybenzylidene]tetrahydrofuran-2-one ,  (3R)-3α-(1,3-Benzodioxole-5-ylmethyl)-4α-hydroxy-4-isopropyl-5-[(Z)-4-methoxybenzylidene]tetrahydrofuran-2-one

Reference (12)：

• 1) Mason, C., Edwards, K., Carlson, R., Pignatello, J., Gleason, F., and Wood, J., Isolation of chlorine-containing antibiotic from the freshwater cyanobacterium Scytonema hofmanni. Science, 215, 400-402 (1982).
• 2) Gleason, F., and Case, D., Activity of the natural algicide, cyanobacterin, on angiosperms. Plant Physiol., 80, 834-837 (1986).
• 3) Gleason, F., Case, D., Sipprell, K., and Magnuson, T., Effect of the natural algicide, cyanobacterin, on a herbicide-resistant mutant of Anacystis nidulans R2. Plant Science, 46, 5-10 (1986).
• 4) Jong, T., Williard, P., and Porwoll, J., Total synthesis and X-ray structure determination of cyanobacterin. J. Org. Chem., 49, 735-736 (1984).
• 5) Gleason, F., and Paulson, L., Site of action of the natural algicide, cyanobacterin, in the blue-green alga, Synechococcus sp. Arch. Microbiol., 138, 273-277 (1984).

Terms in the title (7)： シアノバクテリン ,  立体異性体 ,  系統 ,  戦略 ,  エピマ ,  非対称 ,  全合成