Abstract
In the fused tetra-cyclic system of the title compound, C29H36O9, the five-membered dioxolane ring adopts a twist conformation; the two adjacent C atoms deviate alternately from the mean plane of the other three atoms by -0.252 (6) and 0.340 (6) Å. The cyclo-hexane, cyclo-hexene and central cyclo-octane rings show chair, half-chair and boat-chair forms, respectively. There are three intra-molecular C-H⋯O inter-actions supporting the mol-ecular conformation, with one S(6) and two S(7) graph-set motifs. In the crystal, inter-molecular O-H⋯O hydrogen bonds connect the mol-ecules into a helical chain running along the c-axis direction, generating a C(7) graph-set motif. The chains are further linked by inter-molecular C-H⋯O inter-actions to construct a three-dimensional network. There is no valid C-H⋯π inter-action.
Highlights
In the fused tetracyclic system of the title compound, C29H36O9, the fivemembered dioxolane ring adopts a twist conformation; the two adjacent C atoms deviate alternately from the mean plane of the other three atoms by À0.252 (6) and 0.340 (6) A
The chains are further linked by intermolecular C—HÁ Á ÁO interactions to construct a three-dimensional network
The title compound, which has a fused tetracyclic core composed of a taxane skeleton with an external cyclic carbonate, was afforded as a chiral form in an improved synthesis of paclitaxel (Iiyama et al, 2021)
Summary
Paclitaxel (systematic name: (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetoxy-1,9-dihydroxy-15-{[(2R,3S)-3-benzoylamino-2-hydroxy-3-phenyl]propanoyl}oxy-10,14,17,17-tetramethyl-11-oxo-6-oxa-tetracyclo[11.3.1.03,10.04,7]heptadec-13en-2-yl benzoate) is a well-known natural diterpenoid containing a taxane framework (tricyclo[9.3.1.03,8]pentadecane; Fig. 1), with potent antitumor activity (Wall & Wani, 1995). Its highly complicated structure and significant bioactivity have attracted wide chemical and medicinal interest. The title compound, which has a fused tetracyclic core composed of a taxane skeleton with an external cyclic carbonate, was afforded as a chiral form in an improved synthesis of paclitaxel (Iiyama et al, 2021). Several closely related structures (Oishi, Yamaguchi et al, 2015; Oishi, Fukaya et al, 2015a,b) obtained in another synthetic pathway (Fukaya, Tanaka et al, 2015; Fukaya, Kodama et al, 2015) have been reported previously as racemic crystals
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