Art

J-GLOBAL ID：200902169575917530   Reference number：02A0035867

Total Synthesis of Capsanthin Using Lewis Acid-Promoted Regio- and Stereoselective Rearrangement of Tetrasubstituted Epoxide.

四置換エポキシドのLewis酸促進位置及び立体選択的転位反応を用いるカプサンチンの全合成

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： 49  Issue： 12  Page： 1662-1663  Publication year： Dec. 01, 2001 
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： *carotenoid ,...
Semi thesaurus term： Capsicum annuum

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JST classification (2)： Carotenoids,other terpenoids  (CF10025Z) ,  Rearrangement reaction,isomerization  (CF02070E)

Substance index (17)： Capsanthin ,  Crassostreaxanthin B ,  Mytiloxanthin ,  3,3,5-Trimethyl-4-ethynyl-4-cyclohexene-1β-ol ,  (R)-3,5,5-Trimethyl-4-[(E)-2-(tributylstannyl)ethenyl]-3-cyclohexene-1α-ol ,  (2E,4E)-3-Methyl-5-[(4R)-2,6,6-trimethyl-4β-hydroxy-1-cyclohexenyl]-2,4-pentadienoic acid ethyl ester ,  (2E,4E)-3-Methyl-5-[(4R)-2,6,6-trimethyl-4β-(tert-butyldimethylsiloxy)-1-cyclohexenyl]-2,4-pentadienoic acid ethyl ester ,  (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 ,  (2E,4E)-3-Methyl-5-[(1R)-2,2,6β-trimethyl-4α-(tert-butyldimethylsiloxy)-7-oxabicyclo[4.1.0]heptane-1β-yl]-2,4-pentadienoic acid ethyl ester ,  (2E,4E)-3-Methyl-5-[(1S)-2,2,6α-trimethyl-4α-(tert-butyldimethylsiloxy)-7-oxabicyclo[4.1.0]heptane-1α-yl]-2,4-pentadienal ,  (2E,4E)-3-Methyl-6-oxo-6-[(1R)-1,2,2-trimethyl-4-hydroxycyclopentane-1β-yl]-2,4-hexadienal ,  (2E,4E,6E,8E,10E,12E)-2,7,11-Trimethyl-14-oxo-14-[(1R)-1,2,2-trimethyl-4-hydroxycyclopentane-1β-yl]tetradeca-2,4,6,8,10,12-hexene-1-al ,  (2E,4E,6E,8Z,10E,12E)-2,7,11-Trimethyl-14-oxo-14-[(1R)-1,2,2-trimethyl-4-hydroxycyclopentane-1β-yl]tetradeca-2,4,6,8,10,12-hexene-1-al ,  (2E,4E,6Z,8E,10E,12E)-2,7,11-Trimethyl-14-oxo-14-[(1R)-1,2,2-trimethyl-4-hydroxycyclopentane-1β-yl]tetradeca-2,4,6,8,10,12-hexene-1-al ,  3-(Trifluoromethylsulfonyloxy)isocrotonic acid ethyl ester ,  Triphenyl[(2E,4E,6E)-2,7-dimethyl-8,8-dimethoxy-2,4,6-octatrienyl]phosphonium ,  [(2E,4E)-3-Methyl-5-[(R)-2,6,6-trimethyl-4β-hydroxy-1-cyclohexenyl]-2,4-pentadienyl]triphenylphosphonium

Reference (22)：

• 1) a) Tode C., Yamano Y., Ito M., J. Chem. Soc., Perkin Trans. 1, 1999, 1625-1626
•  b) Idem, Chem. Pharm. Bull., 48, 1833-1834 (2000).
• 2) a) Yamano Y., Tode C., Ito M., J. Chem. Soc., Perkin Trans. 1, 1996, 1337-1339
•  b) Idem, ibid., 1998, 2569-2581.
• 3) We have employed the numbering system used in carotenoids.

Terms in the title (8)： 置換 ,  エポキシド ,  Lewis酸 ,  促進 ,  立体 ,  転位反応 ,  カプサンチン ,  全合成