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 taxoids, identified as N-debenzoyl-N-butanoyl taxol [1] and 7 beta-acetoxy-9-acetylspicataxine [2a]. A new baccatin IV derivative [7a] and the lignans hydroxymatairesinol [8] and (-)-epinortrachelogenin [9] were also isolated. The epoxidation of Delta(4(20),11) taxadienes was investigated, disclosing an unusual reactivity of the bridgehead double-bond towards peracids. Regiochemically and stereochemically unnatural epoxides of taxoids were obtained. Nmr data for these compounds were compared with literature values on the natural epoxides. No significant correlation between the configuration of the 4(20)-oxirane ring and the chemical shift of H-5 was found.