Art

J-GLOBAL ID：201002229513353154   Reference number：10A0052305

ENANTIOSELECTIVE TOTAL SYNTHESIS OF NOVEL DITERPENOID PYRONES (+)-SESQUICILLIN AND (-)-NALANTHALIDE FROM FUNGAL FERMENTATIONS

真菌類の発酵から得た新規なジテルペノイドピロン(+)-セスキシリン及び(-)-ナランタリドのエナンチオ選択的全合成

Author (4)： OGUCHI Takamasa (Tohoku Pharmaceutical Univ., Sendai, JPN) ,  WATANABE Kazuhiro (Tohoku Pharmaceutical Univ., Sendai, JPN) ,  ABE Hideki (Tohoku Pharmaceutical Univ., Sendai, JPN) ,  KATOH Tadashi (Tohoku Pharmaceutical Univ., Sendai, JPN)
Material： Heterocycles  (International Journal for Reviews and Communications in Heterocyclic Chemistry)
Volume： 80  Issue： 1  Page： 229-250  Publication year： Jan. 01, 2010 
JST Material Number： S0966A  ISSN： 0385-5414  CODEN： HTCYAM  Document type： Article
Article type： 原著論文  Country of issue： Japan (JPN)  Language： ENGLISH (EN)

Thesaurus term： total synthesis ,...
Semi thesaurus term： Acremonium ,...

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JST classification (2)： Diterpenes,sesterterpenes  (CF10023R) ,  Basic research of antitumor(=antineoplastic)drugs  (GW16010A)

Substance index (11)： (-)-Nalanthalide ,  Sesquicillin A ,  Wieland-Miescher ketone ,  (5S,4aα)-1,1-[Ethylenebis(oxy)]-5,8aβ-dimethyl-5α-allyldecalin-6-one ,  5α-(4-Methyl-3-pentenyl)-6β-(tert-butyldimethylsiloxy)-2-[(tributylstannyl)methoxymethyl]-5,8aβ-dimethyl-3,4,4aα,5,6,7,8,8a-octahydronaphthalene ,  (1R,4aα)-2-Methylene-5,8aβ-dimethyl-5α-(4-methyl-3-pentenyl)-6β-(tert-butyldimethylsiloxy)decalin-1α-methanol ,  (4aα)-5α-(4-Methyl-3-pentenyl)-6β-(tert-butyldimethylsiloxy)-2-methylene-5,8aβ-dimethyldecalin-1α-carbaldehyde ,  2-Methoxy-3-[hydroxy[(1R,4aα)-2-methylene-5,8aβ-dimethyl-5α-(4-methyl-3-pentenyl)-6β-(tert-butyldimethylsiloxy)decalin-1α-yl]methyl]-5,6-dimethyl-4H-pyran-4-one ,  2-Methoxy-3-[[(1R,4aα)-2-methylene-5,8aβ-dimethyl-5α-(4-methyl-3-pentenyl)-6β-hydroxydecalin-1α-yl]methyl]-5,6-dimethyl-4H-pyran-4-one ,  MF-3 ,  2-Methoxy-3-bromo-5,6-dimethyl-4H-pyran-4-one

Reference (18)：

• Viridoxins A and B, see: S. Gupta, S. B. Krasnoff, J. A. A. Renwick, D. W. Roberts, J. R. Steiner, and J. Clardy, J. Org. Chem., 1993, 58, 1062.
• Sesquicillins, see:(a) B. Engel, G. Erkel, T. Anke, and O. Sterner, J. Antibiot., 1998, 51, 518;(b) H.-W. Jeong, H.-J. Lee, Y.-H. Kho, K.-H. Son, M. Y. Han, J.-S. Lim, M.-Y. Lee, D. C. Han, J.-H. Ha, and B.-M. Kwon, Bioorg. Med. Chem., 2002, 10, 3129;(c) R. Uchida, R. Imasato, Y. Yamaguchi, R. Masuma, K. Shiomi, H. Tomoda, and S. Ōmura, J. Antibiot., 2005, 58, 397. Sesquicillin (1) has been previously reported in patent literature, however, the structural elucidation has not been described;(d) T. B. Hirschthal and T. H. Neuallschwil (Sandoz Ltd., Switzerland), DE 2, 316, 429, October 11, 1973;(e) A. Kuwabara, S. Fujita, S. Kobayashi, and T. Nishigori (Nippon Kayaku K. K. Japan), JP 8, 092, 119, April 9, 1996.
• Subglutinols A and B, see: J. C. Lee, E. Lobkovsky, N. B. Pliam, G. Strobel, and J. Clardy, J. Org. Chem., 1995, 60, 7076.
• Nalanthalide, see: M. A. Goetz, D. L. Zink, G. Denzeny, A. Dombrowski, J. D. Polishook, J. P. Felix, R. S. Slaughter, and S. B. Singh, Tetrahedron Lett., 2001, 42, 1255.
• Candelalides A-C, see: S. B. Singh, D. L. Zink, A. W. Dombrowski, G. Dezeny, G. F. Bills, J. P. Felix, R. S. Slaughter and M. A. Goetz, Org. Lett., 2001, 3, 247.

Terms in the title (5)： 真菌類 ,  発酵 ,  セスキシリン ,  ナランタリド ,  全合成