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J-GLOBAL ID：200902192325698495   Reference number：98A0906376

Total Syntheses of (±)-Phycocyanobilin and Its Derivatives Bearing a Photoreactive Group at D-ring.

D環に光反応性基を有する(±)-フィコシアノビリン及びその誘導体の全合成

Author (8)： KAKIUCHI T (Kanazawa Univ., Ishikawa) ,  KATO H (Kanazawa Univ., Ishikawa) ,  JAYASUNDERA K P (Kanazawa Univ., Ishikawa) ,  HIGASHI T (Kanazawa Univ., Ishikawa) ,  WATABE K (Kanazawa Univ., Ishikawa) ,  SAWAMOTO D (Kanazawa Univ., Ishikawa) ,  KINOSHITA H (Kanazawa Univ., Ishikawa) ,  INOMATA K (Kanazawa Univ., Ishikawa)
Material： Chemistry Letters  (Chem Lett)
Issue： 10  Page： 1001-1002  Publication year： Oct. 1998 
JST Material Number： S0742A  ISSN： 0366-7022  CODEN： CMLTAG  Document type： Article
Article type： 短報  Country of issue： Japan (JPN)  Language： ENGLISH (EN)

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

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JST classification (1)： Pyrroles  (CF07076L)

Substance index (24)： Phycocyanobilin ,  (2R,3E)-18-Ethyl-3-ethylidene-1,2,3,19,22,24-hexahydro-2,7,13-trimethyl-17-[4-[3-(trifluoromethyl)-3H-diazirine-3-yl]phenyl]-1,19-dioxo-21H-biline-8,12-dipropanoic acid ,  (2R)-1,19-Dioxo-2,7,13,17-tetramethyl-3-[(E)-ethylidene]-18-[4-[3-(trifluoromethyl)-3H-diazirine-3-yl]phenyl]-1,2,3,19,22,24-hexahydro-21H-biline-8,12-dipropanoic acid ,  Maleic acid anhydride ,  3-Methyl-2,5-furandione ,  3-Methyl-4-ethylidene-5-thioxopyrrolidin-2-one ,  2-(tert-Butoxycarbonyl)-4-methyl-5-[1-(triphenylphosphoranylidene)-2-oxo-2-(allyloxy)ethyl]-1H-pyrrole-3-propionic acid allyl ester ,  2-(tert-Butoxycarbonyl)-4-methyl-1H-pyrrole-3-propionic acid methyl ester ,  2-(tert-Butoxycarbonyl)-4-methyl-1H-pyrrole-3-propanoic acid allyl ester ,  2-(tert-Butoxycarbonyl)-4-methyl-5-formyl-1H-pyrrole-3-propionic acid allyl ester ,  2-(tert-Butoxycarbonyl)-4-methyl-5-[1-(3-ethylidene-4-methyl-5-oxopyrrolidine-2-ylidene)-2-oxo-2-(allyloxy)ethyl]-1H-pyrrole-3-propionic acid allyl ester ,  2-Formyl-4-methyl-5-[1-(3-ethylidene-4-methyl-5-oxopyrrolidine-2-ylidene)-2-oxo-2-(allyloxy)ethyl]-1H-pyrrole-3-propionic acid allyl ester ,  3-Ethyl-4-methyl-5-tosyl-3-pyrroline-2-one ,  3-Ethyl-4-[4-[3-(trifluoromethyl)-3H-diazirine-3-yl]phenyl]-5-tosyl-3-pyrroline-2-one ,  3-[4-[3-(Trifluoromethyl)-3H-diazirine-3-yl]phenyl]-4-methyl-5-tosyl-3-pyrroline-2-one ,  2-(tert-Butoxycarbonyl)-4-methyl-5-(3-methyl-4-ethyl-5-oxopyrrolidine-2-ylidenemethyl)-1H-pyrrole-3-propionic acid allyl ester ,  2-(tert-Butoxycarbonyl)-4-methyl-5-[3-[4-[3-(trifluoromethyl)-3H-diazirine-3-yl]phenyl]-4-ethyl-5-oxopyrrolidine-2-ylidenemethyl]-1H-pyrrole-3-propionic acid allyl ester ,  2-(tert-Butoxycarbonyl)-4-methyl-5-[3-methyl-4-[4-[3-(trifluoromethyl)-3H-diazirine-3-yl]phenyl]-5-oxopyrrolidine-2-ylidenemethyl]-1H-pyrrole-3-propionic acid allyl ester ,  4-Methyl-5-(3-methyl-4-ethyl-5-oxopyrrolidine-2-ylidenemethyl)-1H-pyrrole-3-propionic acid allyl ester ,  4-Methyl-5-[3-[4-[3-(trifluoromethyl)-3H-diazirine-3-yl]phenyl]-4-ethyl-5-oxopyrrolidine-2-ylidenemethyl]-1H-pyrrole-3-propionic acid allyl ester ,  4-Methyl-5-[3-methyl-4-[4-[3-(trifluoromethyl)-3H-diazirine-3-yl]phenyl]-5-oxopyrrolidine-2-ylidenemethyl]-1H-pyrrole-3-propionic acid allyl ester ,  (2R)-1,19-Dioxo-2,7,13,17-tetramethyl-3-[(E)-ethylidene]-5-(allyloxycarbonyl)-18-ethyl-1,2,3,19,22,24-hexahydro-21H-biline-8,12-dipropanoic acid diallyl ester ,  (2R)-1,19-Dioxo-2,7,13-trimethyl-3-[(E)-ethylidene]-5-(allyloxycarbonyl)-17-[4-[3-(trifluoromethyl)-3H-diazirine-3-yl]phenyl]-18-ethyl-1,2,3,19,22,24-hexahydro-21H-biline-8,12-dipropanoic acid diallyl ester ,  (2R)-1,19-Dioxo-2,7,13,17-tetramethyl-3-[(E)-ethylidene]-5-(allyloxycarbonyl)-18-[4-[3-(trifluoromethyl)-3H-diazirine-3-yl]phenyl]-1,2,3,19,22,24-hexahydro-21H-biline-8,12-dipropanoic acid diallyl ester

Reference (17)：

• 1) P. Schmidt, U. Westphal, K. Worm, S. E. Braslavsky, W. Gärtner, and K. Schaffner, J. Photochem. Photobiol. B : Biology, 34, 73 (1996), and references cited therein.
• 2) a) A. Gossaure and R.-P. Hinze, J. Org. Chem., 43, 283 (1978).
•  b) J.-P. Weller and A. Gossauer, Chem. Ber., 113, 1603 (1980).
• 3) a) K. Kohori, M. Hashimoto, H. Kinoshita, and K. Inomata, Bull. Chem. Soc. Jpn., 67, 3088 (1994).
•  b) H. Ngwe, E. Nakayama, T. Higashi, H. Kinoshita, and K. Inomata, Chem. Lett., 1995, 713.

Terms in the title (5)： 環 ,  反応性基 ,  フィコシアノビリン ,  誘導体 ,  全合成