摘要 |
FIELD: chemistry.SUBSTANCE: present invention relates to method of producing ingenol-3-angelate (I) from ingenol (II). Invention also relates to intermediate products used for synthesis of ingenol-3-angelate (I) from ingenol (II), and methods of producing said intermediate products. Method of producing ingenol-3-angelate (1aR,2S,5R,5aS,6S,8aS,9R,10aR)-5,5a-dihydroxy-4-(hydroxymethyl)-1,1,7,9-tetramethyl-11-oxo-1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8A-methanocyclopente[a]cycloprope[e]cyclodecen-6-yl ester 2-methyl-2(Z)-butenoic acid) of formula (I) from ingenol of formula (II) includes following steps: (a) reaction of one or both of hydroxyl groups in positions 5 and 20 ingenol with suitable hydroxyl protecting agents, which can be identical or different, to obtain compound of general formula (III) or (IV) in which Rrepresents hydrogen or hydroxyl protecting group and Rrepresents hydrogen or hydroxyl protecting group, provided that Rand Rsimultaneously represent hydrogen, or in which D is hydroxyl protecting group, (b) esterification hydroxyl group in position 3 compounds (III) or (IV) to obtain compounds of general formula (V) or (VI), in which R, Rand D have values given above, and (c) removing hydroxyl protecting groups Ror R, or Ror R, or the compounds (V) or (VI) to obtain ingenol-3-angelate of formula (I).EFFECT: method allows to produce end product with good output.25 cl, 11 tbl, 29 ex |