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Total Synthesis and Determina2on of the Absolute Configura2on of 5,6Dihydroαpyrone Natural Product Synargentolide B Kavirayani R. Prasad and Phaneendra Gutala J. Org. Chem. 2013, 78, 3313–3322 Mustafa Kazancioglu Current Literature 20 April 2013 Mustafa Kazancioglu @ Wipf Group Page 1 of 10 4/21/2013
Transcript of TotalSynthesisandDeterminaonoftheAbsolute …ccc.chem.pitt.edu/wipf/Current...
Total Synthesis and Determina2on of the Absolute Configura2on of 5,6-‐Dihydro-‐α-‐pyrone Natural Product
Synargentolide B Kavirayani R. Prasad and Phaneendra Gutala
J. Org. Chem. 2013, 78, 3313–3322
Mustafa Kazancioglu Current Literature 20 April 2013
Mustafa Kazancioglu @ Wipf Group Page 1 of 10 4/21/2013
• Synargentolide B is such a pyrone isolated from Syncolostemon argenteus by RiveC’s group in 1998 along with other synargentolides A, C, D, and E. • Also, a natural product isolated in 1990 by Pereda-‐Miranda et al., nine years prior to the isolaNon of Synargentolide B, whose structure was proposed based on the natural product 4-‐deacetoxy-‐10-‐epi-‐olguine, proved to be idenNcal to Synargentolide B as shown by the synthesis of Prasad and Gutala. • They exhibit a range of potent biological properNes, anNcancer acNvity, cytotoxic and anN-‐tumor. • Also, they inhibit HIV protease, induce apoptosis, and have proven to be anN-‐leukemic, along with having many other relevant pharmacological properNes.
Sabitha, G.; Gopal, P.; Reddy, C. N.;Yadav, J. S. Tetrahedron Le.. 2009, 50, 6298. Marco, J. A.; Carda, M.; Murga, J.; Falomir, E. Tetrahedron 2007, 63, 2929. Prasad, K. R.; Penchalaiah, K. J. Org. Chem. 2011, 76, 6889.
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Retrosynthesis for the Synthesis of Diasterreomers 1a-‐d
Prasad, K. R.; Penchalaiah, K. J. Org. Chem. 2011, 76, 6889.
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Synthesis of the Diastereomer 1a:
Prasad, K. R.; Penchalaiah, K. J. Org. Chem. 2011, 76, 6889.
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Prasad, K. R.; Penchalaiah, K. J. Org. Chem. 2011, 76, 6889.
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Synthesis of the Diastereomer 1b:
Prasad, K. R.; Penchalaiah, K. J. Org. Chem. 2011, 76, 6889.
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Synthesis of the Acetals 21c and 21d and the diastereomers 1c and 1d:
Prasad, K. R.; Penchalaiah, K. J. Org. Chem. 2011, 76, 6889.
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7 Prasad, K. R.; Penchalaiah, K. J. Org. Chem. 2011, 76, 6889.
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In conclusion:
• Total synthesis of Synargentolide B(1a-‐d) was achieved. • The absolute stereochemistry was determinated by X-‐ray crytal structure of the corresponding acetate 7. • One of the diastereomers (1d) NMR spectral date was in agreement with previous works.
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