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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 48, 2018 - Issue 17
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Articles

Enantioselective total syntheses of (−)-clavaminol A and deacetyl (+)-clavaminol H

Rachana PandeySchool of Chemistry and Biochemistry, Thapar Institute of Engineering and Technology, Patiala, India; View further author information
,
Anju GehlawatSchool of Chemistry and Biochemistry, Thapar Institute of Engineering and Technology, Patiala, India; View further author information
,
Ranjana PrakashSchool of Chemistry and Biochemistry, Thapar Institute of Engineering and Technology, Patiala, India; Correspondence[email protected]
View further author information
&
Satyendra Kumar PandeySchool of Chemistry and Biochemistry, Thapar Institute of Engineering and Technology, Patiala, India; ;Department of Chemistry, Institute of Science, Banaras Hindu University, Varanasi, IndiaCorrespondence[email protected]
ORCID Iconhttp://orcid.org/0000-0001-7839-567XView further author information
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Pages 2280-2287 | Received 14 May 2018, Published online: 10 Aug 2018

References

  • (a) Menna, M. Phytochem. Rev. 2009, 8, 461. doi: 10.1007/s11101-009-9131-y. (b) Pruett, S. T.; Bushnev, A.; Hagedorn, K.; Adiga, M.; Haynes, C. A.; Sullards, M. C.; Liotta, D. C.; Merrill, A. H. J. Lipid Res. 2008, 49, 1621. doi: 10.1194/jlr.R800012-JLR200. (c) Brodesser, S.; Sawatzki, P.; Kolter, T. Eur. J. Org. Chem. 2003, 2003, 2021. doi: 10.1002/ejoc.200200518. (d) Bergmeier, S. C. Tetrahedron 2000, 56, 2561. doi: 10.1016/S0040-4020(00)00149-6. (e) Kobayashi, S.; Furuta, T.; Hayashi, T.; Nishijima, M.; Hanada, K. J. Am. Chem. Soc. 1998, 120, 908. doi: 10.1021/Ja9855040. (f) Kamitakahara, H.; Suzuki, T.; Nishigori, N.; Suzuki, Y.; Kanie, O.; Wong, C. H. Angew. Chem. Int. Ed. Engl. 1998, 37, 1524 doi: 10.1002/(SICI)1521-3773(19980619)37:11<1524::AID-ANIE1524>3.0.CO;2-D. (g) Kobayashi, E.; Motoki, K.; Yamaguchi, Y.; Uchida, T.; Fukushima, H.; Koezuka, Y. Bioorg. Med. Chem 1996, 4, 615. (h) Li, H. Y.; Matsunaga, S.; Fusetani, N. Tetrahedron 1995, 51, 2273. doi: 10.1016/0040-4020(94)01097-J. (i) Natori, T.; Morita, M.; Akimoto, K.; Koezuka, Y. Tetrahedron 1994, 50, 2771. doi: 10.1016/S0040-4020(01)86991-X. (j) Higuchi, R.; Inukai, K.; Jhou, J. X.; Honda, M.; Komori, T.; Tsuji, S.; Nagai, Y. Liebigs Ann. Chem. 1993, 1993, 359. doi: 10.1002/jlac.199319930161.
  • (a) Aiello, A.; Fattorusso, E.; Giordano, A.; Menna, M.; Navarrete, C.; Munoz, E. Tetrahedron 2009, 65, 4384. doi: 10.1016/j.tet.2009.03.056.
  • Clavaminol A has an IC50 value of approximately 5 mg mL−1 against AGS cells. It has a similar level of cytotoxicity against T47D and A549 cells.
  • (a) Jin, T.; Zhao, L.; Huang, M.; Yue, Y.; Zheng, Z.-B.; Ham, W.-H. Tetrahedron: Asymmetry 2017, 28, 725. doi: 10.1016/j.tetasy.2017.04.004.
  • (a) Kaur, A.; Prakash, R.; Pandey, S. K. ChemistrySelect 2018, 3, 105. doi: 10.1002/slct.201702732.
  • (a) For reviews on the Swern oxidation, see: Tidwell, T. T. Synthesis 1990, 10, 857. doi: 10.1055/s-1990-27036 (b) Tidwell, T. T. Org. React 1990, 39, 297.
  • Piva, O. Tetrahedron 1994, 50, 13687. doi: 10.1016/S0040-4020(01)85681-7.
  • (a) Becker, H.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 448. (b) Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483. (c) Torri, S.; Liu, P.; Bhuvaneswari, N.; Amatore, C.; Jutand, A. J. Org. Chem. 1996, 61, 3055. doi: 10.1002/anie.199604481.
  • Fernandes, R. A.; Kumar, P. Tetrahedron 2002, 58, 6685. doi: 10.1016/S0040-4020(02)00685-3.
  • MaGee, D. I.; Silk, P. J.; Wu, J.; Mayo, P. D.; Ryall, K. Tetrahedron 2011, 67, 5329. doi: 10.1016/j.tet.2011.05.015.
  • Taber, D. F.; Deker, P. B.; Fales, H. M.; Jones, T. H.; Lloyd, H. A. J. Org. Chem. 1988, 53, 2968. doi: 10.1021/jo00248a013.
  • Fleming, P. R.; Sharpless, K. B. J. Org. Chem. 1991, 56, 2869. doi: 10.1021/jo00008a051.

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