Synthesis of Tri-Substituted Olefin Derivatives from 1-Alkene-1,2-Diboronic Esters via Sequential Suzuki-Suzuki Coupling Reaction and Their Biological Activity

Author:

Kerketta Manoranjan1,Mali Maruti1,Sridhar Gattu12,Sharma Gangavaram V. M.1,Vankudoth Jayaram1

Affiliation:

1. Department of Organic Synthesis & Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad, India

2. Department of Chemistry, Kakatiya Institute of Technology and Science, Warangal, India

Funder

Council for Scientific and Industrial Research

Publisher

Informa UK Limited

Subject

Materials Chemistry,Organic Chemistry,Polymers and Plastics

Reference26 articles.

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2. (a) Robertson, D. W.; Katzenellenbogen, J. A.; Hayes, J. R.; Katzenellenbogen, B. S. “Antiestrogen basicity–activity relationships: a comparison of the estrogen receptor binding and antiuterotrophic potencies of several analogues of (Z)-1,2-diphenyl-1-[4-[2-(dimethylamino)ethoxy]phenyl]-1-butene (tamoxifen, Nolvadex) having altered basicity”. Journal of Medicinal Chemistry 25 (1982): 167. (b) Wu, P.; Wang, L.; Wu, K.; Yu, Z. “Total Synthesis of Kopsinine ”. Organic Letters 17 (2015): 868. (c) Higman, C. S.; Lummiss, J. A. M.; Fogg, D. E. “Olefin Metathesis at the Dawn of Implementation in Pharmaceutical and Specialty- Chemicals Manufacturing”. Angewandte Chemie (International ed. in English) 55 (2016): 3552.

3. (a) Levenson, A. S.; Jordan, V. C. “Selective oestrogen receptor modulation: molecular pharmacology for the millennium”. European Journal of Cancer 35 (1999): 1628. (b) Gigant, N.; Quintin, F.; Bäckvall, J. E. “Preparation of tetrasubstituted olefins using mono or double aerobic direct C-H functionalization strategies: importance of steric effects”. The Journal of Organic Chemistry 80 (2015): 2796. (c) Lim, N.K.; Weiss, P.; Li, B. X.; McCulley, C. H.; Hare, S. R.; Bensema, B. L.; Palazzo, T. A.; Tantillo, D. J.; Zhang, H.M.; Gosselin, F. “Synthesis of Highly Stereodefined Tetrasubstituted Acyclic All-carbon Olefins via a syn-Elimination Approach”. Organic Letters 19 (2017): 6212.

4. Bhatt, S.; Stender, J. D.; Joshi, S.; Wu, G.; Katzenellenbogen, B. S. “OCT-4: a novel estrogen receptor-α collaborator that promotes tamoxifen resistance in breast cancer cells”. Oncogene 35 (2016): 5722. (c) Kortman, G. D.; Hull, K. L. “Copper-Catalyzed Hydroarylation of Internal Alkynes: Highly Regio- and Diastereoselective Synthesis of 1,1-Diaryl, Trisubstituted Olefins”. ACS Catalysis 7 (2017): 6220.

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