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Synthesis and Crystal Studies of Novel 11,12-Dihydro-Taxoids Derived from 1-Deoxybaccatin VI

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Abstract

Two novel taxoids were synthesized from 1-deoxybacctin VI (1) and their crystal structures were determined by X-ray crystallographic techniques. The influence of the 11,12-olefin of the tetracyclic moiety on molecular conformations were investigated. Comparison to other baccatin analogs, a larger effect on the conformation of the diterpenoid core is observed when the 11,12-olefin is reducted. Conformational analysis show that the reduction of the 11,12-olefin has a decisive influence on the conformation of the A and B ring. Compounds 3 and 5 crystallize in orthorhombic system, space group P212121. In the structure of compound 3, the six-membered A ring exhibits the 1,3-diplanar boat conformation, the eight-membered B ring adopts a boat–chair conformation, and the six-membered C ring exhibits a slightly distorted half-chair conformation. However, in 11,12-dihydro-taxoids 5, the six-membered A ring exhibits a chair conformation and the conformation of the eightmembered B ring has a large distortion.

Graphical Abstract

The synthesis of novel 11,12-dihydro-taxoids from 1-deoxybacctin VI are presented, in which the crystal structure of the compound 5 was characterized.

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Fig. 1
Scheme 1
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Date Availability

Crystallographic data (excluding structure factors) for the structures 3 and 5 have been deposited with the Cam-bridge Crystallographic Data Centre as supplementary publication nos. CCDC 2128772 (3), CCDC 2128773 (5). Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK [Fax: (internet.) + 44–1223/336–033; E-mail: deposit@ccdc.cam.ac.uk].

Abbreviations

DFV-OTX:

3’-Difluorovinyl-ortataxel

TNBC:

Triple-negative breast cancer

t-BuO:

Tert-butoxycarbonyl

2,2-DMP:

2,2-Dimethoxypropane

NMO:

4-Methylmorpholine N-oxide

TPAP:

Tetrapropylammonium Perruthenate

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Acknowledgements

The authors are grateful for support from the National Natural Science Foundation of China (Project No. 21272154). The work is also in part supported by Science and Technology Commission of Shanghai Municipality (Grant No. 19ZR1419700).

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  1. Department of Chemistry, College of Sciences, Shanghai University, 99 Shangda Road, Baoshan District, Shanghai, 200444, People’s Republic of China

    Ye-Sha Cui, Ping Tang, Yong-Mei Cui, Ling-Yun Yue & Hai-Xia Lin

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  1. Ye-Sha Cui
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Cui, YS., Tang, P., Cui, YM. et al. Synthesis and Crystal Studies of Novel 11,12-Dihydro-Taxoids Derived from 1-Deoxybaccatin VI. J Chem Crystallogr 53, 117–126 (2023). https://doi.org/10.1007/s10870-022-00947-z

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