THE CHEMISTRY AND OCCURRENCE OF TAXANE DERIVATIVES .14. TAXOIDS FROM THE ROOTS OF TAXUS X MEDIA CV HICKSII

The roots of Taxus X media cv. Hicksii gave two new pseudoalkaloidal t axoids, identified as N-debenzoyl-N-butanoyl taxol [1] and 7 beta-acet oxy-9-acetylspicataxine [2a]. A new baccatin IV derivative [7a] and th e lignans hydroxymatairesinol [8] and (-)-epinortrachelogenin [9] were also isolated. The epoxidation of Delta(4(20),11) taxadienes was inve stigated, disclosing an unusual reactivity of the bridgehead double-bo nd towards peracids. Regiochemically and stereochemically unnatural ep oxides of taxoids were obtained. Nmr data for these compounds were com pared with literature values on the natural epoxides. No significant c orrelation between the configuration of the 4(20)-oxirane ring and the chemical shift of H-5 was found.