Abstract
Three novel taxoids were synthesized from 1-deoxybaccatinVI and their crystal structures were determined by X-ray crystallographic techniques. The influence of C(7), C(10) and C(4) substituents of the tetracyclic moiety on molecular conformations were investigated. The result shows that 4-acetyl moiety plays an important role in the conformation of the diterpenoid core. All of these 1-deoxybaccatinVI derivatives crystallize in orthorhombic system, space group P212121. In the structures, the six-membered A ring exhibits the 1,4-di-planar conformation, the eight-membered B ring adopts boat–chair conformation and the six-membered C ring exhibits slightly distorted half-chair conformation.
Graphical Abstract
Three novel taxoids (compounds 2, 4, 5) were synthesized from 1-deoxybaccatinVI and the differences in their crystal structures have been discussed.
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Acknowledgments
The authors are grateful for support from the National Natural Science Foundation of China (Project No. 30672506), Leading Academic Discipline Project of Shanghai Municipal Education Commission (Project No. J50102), and Shanghai Pujiang Program (No. 10PJ1403700).
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Hu, FL., Han, N., Yu, J. et al. Synthesis and Structural Studies of Novel Taxoids Derived from 1-DeoxybaccatinVI. J Chem Crystallogr 41, 1586–1592 (2011). https://doi.org/10.1007/s10870-011-0144-1
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DOI: https://doi.org/10.1007/s10870-011-0144-1