Art

J-GLOBAL ID：200902256857503011   Reference number：03A0782005

Systematic Strategy for the Synthesis of Cyanobacterin and Its Stereoisomers. 1. Asymmetric Total Synthesis of Dechloro-cyanobacterin and Its Enantiomer

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 1. 脱クロロ-シアノバクテリンおよびそのエナンチオマの非対称全合成

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： 2183-2193  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 (9)： Cyanobacterin ,  (4S)-3-[3-(1,3-Benzodioxole-5-yl)propionyl]-4-benzyloxazolidine-2-one ,  (2S,3R)-2-(1,3-Benzodioxole-5-ylmethyl)-5-(4-methoxyphenyl)-4-pentyne-1,3-diol ,  (2S,3S)-2-(1,3-Benzodioxole-5-ylmethyl)-5-(4-methoxyphenyl)-4-pentyne-1,3-diol ,  (2R,3S)-2-(1,3-Benzodioxole-5-ylmethyl)-5-(4-methoxyphenyl)-4-pentyne-1,3-diol ,  (4S)-1-(4-Methoxyphenyl)-4-(1,3-benzodioxole-5-ylmethyl)-5-hydroxy-1-pentene-3-one ,  (4R)-1-(4-Methoxyphenyl)-4-(1,3-benzodioxole-5-ylmethyl)-5-hydroxy-1-pentene-3-one ,  (3R)-3α-(1,3-Benzodioxole-5-ylmethyl)-4β-hydroxy-4-isopropyl-5-[(Z)-4-methoxybenzylidene]tetrahydrofuran-2-one ,  (3S)-3β-(1,3-Benzodioxole-5-ylmethyl)-4α-hydroxy-4-isopropyl-5-[(Z)-4-methoxybenzylidene]tetrahydrofuran-2-one

Reference (20)：

• 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) Pignatello, J., Porwoll, J., Carlson, R., Xavier, A., Gleason, F., and Wood, J., Structure of the antibiotic cyanobacterin, a chlorine-containing γ-lactone from the freshwater cyanobacterium Scytonema hofmanni. J. Org. Chem., 48, 4035-4038 (1983).
• 3) Gleason, F., and Porwoll, J., X-ray structure determination of the naturally occurring isomer of cyanobacterin. J. Org. Chem., 51, 1615-1616 (1986).
• 4) Gleason, F., and Case, D., Activity of the natural algicide, cyanobacterin, on angiosperms. Plant Physiol., 80, 834-837 (1986).
• 5) 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 Sci., 46, 5-10 (1986).

Terms in the title (7)： シアノバクテリン ,  立体異性体 ,  系統 ,  戦略 ,  エナンチオマ ,  非対称 ,  全合成