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1992 (1)
1982 (1)
1Author    Bernd Sorg, Erich HeckerRequires cookie*
 Title    On the Chemistry of Ingenol, III [1] Synthesis of 3-Deoxy-3-oxoingenol, Some 5-Esters and of Ethers and Acetals of Ingenol  
 Abstract    3-Deoxy-3-oxoingenol (3) was prepared from ingenol-5,20-acetonide (25) by oxidation and subsequent removal of the acetonide. 3 was acylated to give homologous 5,20-di-acylates 5-9. From these the 5-monoacylates 14, 15 and 17 were obtained in only moderate yields. Therefore the 20-silyl ether 10 (prepared from 3) was acylated. After smooth removal of the silyl ether the homologous 5-acylates 16. 18 and 19 resulted in good yield. The 5,20-dibutyrate 6 and all 5-acylates prepared (14-19) showed no irritant activity on the mouse ear. The 3-oxo-5-acylates 14-19 could not be reduced to give ingenol-5-acylates (24). Therefore various ingenol derivatives, 29-32, with suitable protected hydroxyl func-tions as well as the corresponding 5-clecanoates 35-38 were synthesized. The protecting groups of the derivatives 35-38 could however not be cleaved off to yield ingenol-5-decanoate (24). 
  Reference    Z. Naturforsch. 37b, 1640—1647 (1982); eingegangen am 2. Juli 1982 
  Published    1982 
  Keywords    Cocarcinogen, Diterpenes, Ingenol Esters, Tumor Promoter 
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 TEI-XML for    default:Reihe_B/37/ZNB-1982-37b-1640.pdf 
 Identifier    ZNB-1982-37b-1640 
 Volume    37 
2Author    H. Roeser, B. Sorg, E. HeckerRequires cookie*
 Title    On the Chemistry of Ingenol, Va. Preparation of Tritium-Labeled 3-O-Tetradecanoylingenol (|20-3H]-3-TI)  
 Abstract    Tritium-labeling o f the ingenol m onoester 3-O-tetradecanoylingenol (3-TI), the prototype tumor promoter o f the ingenane type diterpene esters, is described. The preparation starts with oxidation o f 3-TI by manganese dioxide to yield 3-TI-20-aldehyde which is reduced by [3H]-sodium borohydride in the presence o f equimolar amounts o f cerium trichloride hexahydrate to give [20-3H]-3-TI. The labeled promoter is obtained in 42% overall yield with a specific ra­ dioactivity o f 15.8 Ci/m mol. 
  Reference    Z. Naturforsch. 47b, 1026—1030 (1992); received December 13 1991 
  Published    1992 
  Keywords    Ingenol Ester, Tumor Promoter, Tritium-Labeling 
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 TEI-XML for    default:Reihe_B/47/ZNB-1992-47b-1026.pdf 
 Identifier    ZNB-1992-47b-1026 
 Volume    47