Synthesis of C1–C9 Domain of the Nominal Didemnaketal A
Shunji Zhang
CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Search for more papers by this authorCorresponding Author
Yong Shi
CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, ChinaSearch for more papers by this authorCorresponding Author
Weisheng Tian
CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, ChinaSearch for more papers by this authorShunji Zhang
CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Search for more papers by this authorCorresponding Author
Yong Shi
CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, ChinaSearch for more papers by this authorCorresponding Author
Weisheng Tian
CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, ChinaSearch for more papers by this authorAbstract
Based on chiral pool strategy, a synthesis of the C1–C9 domain of the proposed structure of didemnaketal A, a natural product with potent HIV-1 protease inhibitory activity, has been achieved. Key transformations are a Sharpless asymmetric dihydroxylation and a chelation-controlled allylation.
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REFERENCES
- 1a Potts, B. C. M.; Faulkner, D. J.; Chan, J. A.; Simolike, G. C.; Offen, P.; Hemling, M. E.; Francis, T. A.. J. Am. Chem. Soc., 1991, 113, 6321.
- 1b Pika, J.; Faulkner, D. J.. Nat. Prod. Lett., 1995, 7, 291.
- 1c Salomon, C. E.; Williams, D. H.; Lobkovsky, E.; Clardy, J. C.; Faulkner, D. J.. Org. Lett., 2002, 4, 1699.
- 2a Mohamed, G. A.; Ibrahim, S. R. M.; Badr, J. M.; Youssef, D. T. A.. Tetrahedron, 2014, 70, 35.
- 2b Shaala, L. A.; Youssef, D. T. A.; Ibrahim, S. R. M.; Mohamed, G. A.; Badr, J. M.; Risinger, A. L.; Mooberry, S. L.. Marine Drugs, 2014, 12, 5021.
- 3a Jia, Y. X.; Li, X.; Wu, B.; Zhao, X. Z.; Tu, Y. Q.. Tetrahedron, 2002, 58, 1697.
- 3b Li, X. Q.; Zhao, X. Z.; Liu, P. N.; Tu, Y. Q.. Chin. Chem. Lett., 2004, 15, 757.
- 3c Zhao, X. Z.; Tu, Y. Q.; Peng, L.; Li, X. Q.; Jia, Y. X.. Tetrahedron Lett., 2004, 45, 3713.
- 3d Li, X.-Q.; He, Q.; Tu, Y.-Q.; Zhang, F.-M.; Zhang, S.-Y.. Chin. J. Chem., 2007, 25, 1357.
- 3e Ito, H.; Inoue, T.; Iguchi, K.. Org. Lett., 2008, 10, 3873.
- 3f Fuwa, H.; Noji, S.; Sasaki, M.. Org. Lett., 2010, 12, 5354.
- 4a Zhang, F.-M.; Peng, L.; Li, H.; Ma, A.-J.; Peng, J.-B.; Guo, J.-J.; Yang, D.; Hou, S.-H.; Tu, Y.-Q.; Kitching, W.. Angew. Chem., Int. Ed., 2012, 51, 10846.
- 4b Fuwa, H.; Sekine, K.; Sasaki, M.. Org. Lett., 2013, 15, 3970.
- 5a Peng, L.; Zhang, F.-M.; Yang, B.-M.; Zhang, X.-B.; Liu, W.-X.; Zhang, S.-Y.; Tu, Y.-Q.. Tetrahedron Lett., 2013, 54, 6514.
- 5b Zhang, F.-M.; Tu, Y.-Q.. Tetrahedron Lett., 2014, 55, 3784.
- 6 Fuwa, H.; Muto, T.; Sekine, K.; Sasaki, M.. Chem. Eur. J., 2014, 20, 1848.
- 7a Wang, Z.-K.; Tian, W.-S.; Pan, X.-F.. Acta Chim. Sinica, 2007, 65, 705.
- 7b Wang, Z.-K.; Xu, Q.-H.; Tian, W.-S.; Pan, X.-F.. Tetrahedron Lett., 2007, 48, 7549.
- 7c Wang, Z.-K.; Tian, W.-S.; Pan, X.-F.. Chin. J. Org. Chem., 2007, 25, 866.
- 7d Tian, W.-S.; Shi, Y.. Prog. Chem., 2010, 22, 538.
- 7e Song, Z.-J.; Shi, Y.; Jin, R.-H.; Lin, J.-R.; Tian, W.-S.. Chin. J. Chem., 2012, 30, 2595.
- 7f Zhang, S.-J.; Dong, H.-D.; Gui, J.-S.; Tian, W.-S.. Tetrahedron Lett., 2012, 53, 1882.
- 8 Hercouet, A.; Le Corre, M.. Tetrahedron, 1981, 37, 2867.
- 9 Tian, W.-S.; Liu, S.-S.; Qiu, B.-K.; Wu, X.-J., CN1475494A Chem. Abstr., 2004, 142, 374022.
- 10 Tian, W.-S.; Zhang, S.-J.; Wang, Y., CN102010336A Chem. Abstr., 2011, 474995.
- 11 Amberg, W.; Bennani, Y. L.; Chadha, R. K.; Crispino, G. A.; Davis, W. D.; Hartung, J.; Jeong, K. S.; Ogino, Y.; Shibata, T.; Sharpless, K. B.. J. Org. Chem., 1993, 58, 844.
- 12 Keum, G.; Kang, S. B.; Kim, Y.; Lee, E.. Org. Lett., 2004, 6, 1895.
- 13a Evans, D. A.; Rieger, D. L.; Gage, J. R.. Tetrahedron Lett., 1990, 31, 7099.
- 13b Rychnovsky, S. D.; Skalitzky, D. J.. Tetrahedron Lett., 1990, 31, 945.