Art

J-GLOBAL ID：200902280464642409   Reference number：04A0415878

First Total Synthesis of Cucurbitaxanthin A Applying Regioselective Ring Opening of Tetrasubstituted Epoxides

四置換エポキシドの位置選択的開環を用いるククルビタキサンチンAの初めての全合成

Author (2)： YAMANO Y (Kobe Pharmaceutical Univ., Kobe, JPN) ,  ITO M (Kobe Pharmaceutical Univ., Kobe, JPN)
Material： Chemical and Pharmaceutical Bulletin  (Chemical & Pharmaceutical Bulletin)
Volume： 52  Issue： 6  Page： 780-782  Publication year： Jun. 01, 2004 
JST Material Number： G0504A  ISSN： 0009-2363  CODEN： CPBTAL  Document type： Article
Article type： 短報  Country of issue： Japan (JPN)  Language： ENGLISH (EN)

Thesaurus term： total synthesis ,...
Semi thesaurus term： *carotenoid

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JST classification (1)： Carotenoids,other terpenoids  (CF10025Z)

Substance index (19)： Cucurbitaxanthin A ,  Capsanthin ,  (3S,5R,6S,7E)-5,6-Epoxy-3-hydroxy-7-megastigmen-9-one ,  (2E)-1-[(1R)-1,2,2-Trimethyl-4α-hydroxycyclopentane-1β-yl]-2-pentene-1,4-dione ,  t-Xanthoxin ,  (2E,4E)-6-(1,5,5-Trimethyl-3β-hydroxycyclopentane-1α-yl)-6-oxo-3-methyl-2,4-hexadienal ,  Acetic acid (1S,2E)-1-methyl-3-[(1S,4S,6R)-2,2,6-trimethyl-4-hydroxy-7-oxabicyclo[4.1.0]heptane-1-yl]-2-propenyl ester ,  Acetic acid (1S,2E)-1-methyl-3-[(1R,4S,6R)-2,2,6-trimethyl-6-hydroxy-7-oxabicyclo[2.2.1]heptane-1-yl]-2-propenyl ester ,  Acetic acid 1-[(6S)-4,4,7aα-trimethyl-6α-hydroxy-2,4,5,6,7,7a-hexahydrobenzofuran-2-yl]ethyl ester ,  Acetic acid (2E,4E)-5-[1β,5,5-trimethyl-3β-hydroxy-7-oxabicyclo[4.1.0]heptane-6β-yl]-3-methyl-2,4-pentadienyl ester ,  Acetic acid (2E)-3-[(6S)-4,4,7aα-trimethyl-6α-hydroxy-2,4,5,6,7,7a-hexahydrobenzofuran-2-yl]-2-butenyl ester ,  (2E,4E)-5-[1β,5,5-Trimethyl-3β-hydroxy-7-oxabicyclo[4.1.0]heptane-6β-yl]-3-methyl-2,4-pentadienoic acid ethyl ester ,  (2E,4E)-3-Methyl-5-[(1R,4S,6R)-2,2,6-trimethyl-6-hydroxy-7-oxabicyclo[2.2.1]heptane-1-yl]-2,4-pentadienoic acid ethyl ester ,  (2E)-3-[(6S)-4,4,7aα-Trimethyl-6α-hydroxy-2,4,5,6,7,7a-hexahydrobenzofuran-2-yl]-2-butenoic acid ethyl ester ,  (2E,4E)-5-[1β,5,5-Trimethyl-3β-hydroxy-7-oxabicyclo[4.1.0]heptane-6β-yl]-3-methyl-2,4-pentadienenitrile ,  (2E,4E)-3-Methyl-6-[(1R)-1,2,2-trimethyl-4α-hydroxycyclopentane-1β-yl]-6-oxo-2,4-hexadienenitrile ,  Actinol ,  4α-(tert-Butyldimethylsilyloxy)-2,2,6α-trimethyl-7-oxabicyclo[4.1.0]heptane-1α-carbaldehyde ,  (2E,4E)-3-Methyl-5-[(1S)-2,2,6α-trimethyl-4α-(tert-butyldimethylsiloxy)-7-oxabicyclo[4.1.0]heptane-1α-yl]-2,4-pentadienoic acid ethyl ester

Reference (15)：

• 1) Parkes K. E. B., Pattenden G., Baranyai M., Molnar P., Szabolcs J., Toth G., Tetrahedron Lett., 27, 2535—2538 (1986).
• 2) Deli J., Molnár P., Matus Z., Tóth G., Steck A., Helv. Chim. Acta, 79, 1435—1443 (1996).
• 3) Matsuno T., Tani Y., Maoka T., Matsuo K., Komori T., Phytochemistry, 25, 2837—2840 (1986).
• 4) Yamano Y., Ito M., Chem. Pharm. Bull., 49, 1662—1663 (2001).
• 5) We employed the numbering system used in carotenoids.

Terms in the title (6)： 置換 ,  エポキシド ,  位置選択 ,  開環 ,  ククルビタキサンチンA ,  全合成