STRUCTURE OF SAWARANIN : A DECARBOXYLATED ASCORBIGEN IN THE HEARTWOOD OF CHAMAECYPARIS PISIFERA

Article abstract of DOI:10.1016/0031-9422(88)87047-X

The structure of sawaranin which had been isolated from the heartwood of Chamaecyparis pisifera was reexamined.The structure as a decarboxylated ascorbigen, (3S,4R,6R,7S)-5,8-epoxy-3-p-hydroxyphenyl-5,6,7-trihydroxyoctan-1,4-olide, was determined by spectral analyses of sawaranin and its derivatives and by chemical degradation of monomethylsawaranin into d-p-anisylsuccinic acid an L-threose.Further, sawaranin was synthesized by decarboxylative hydrolysis of the product of the reaction of L-ascorbic acid with methyl 3-hydroxy-3-p-hydroxyphenylpropionate.Key Word Index - Chamaecyparis pisifera; Cupressaceae; heartwood; ascorbigen; sawaranin.