Studies toward the synthesis of three biologically active [5,6]-benzannulated spiroketal natural products are described. The first total synthesis of paecilospirone is reported, employing a late-stage, pH-neutral spiroketalization. A formal synthesis of γ-rubromycin is described, where the spiroketal moiety is formed by delicate manipulation of the electronic properties of the spirocyclization precursor. Finally, model work toward the total synthesis of berkelic acid is summarized, introducing a novel Horner–Wadsworth–Emmons/oxa-Michael (HWE/oxa-M) cascade to access the spiroketal precursor.
Conference
International Symposium on the Chemistry of Natural Products and the 7th International Conference on Biodiversity (ISCNP-27 & ICOB-7), International Conference on Biodiversity, International Symposium on the Chemistry of Natural Products, ICOB, ISCNP, Biodiversity, Natural Products, 27th, Brisbane, Australia, 2011-07-10–2011-07-15
References
1 10.1021/np068054v, D. J. Newman, C. M. Cragg. J. Nat. Prod.70, 461 (2007).Search in Google Scholar PubMed
2a 10.1021/cr050559n, J. E. Aho, P. M. Pihko, T. K. Rissa. Chem. Rev.105, 4406 (2005).Search in Google Scholar PubMed
2b 10.1021/cr00097a015, F. Perron, K. F. Albizati. Chem. Rev.89, 1617 (1989).Search in Google Scholar
3 10.1039/b911514p, J. Sperry, Z. E. Wilson, D. C. K. Rathwell, M. A. Brimble. Nat. Prod. Rep.27, 1117 (2010).Search in Google Scholar PubMed
4 10.1002/anie.200903316, K. Rathwell, S.-H. Yang, K. Y. Tsang, M. A. Brimble. Angew. Chem., Int. Ed.48, 7996 (2009).Search in Google Scholar PubMed
5 T.-Y. Yuen, S.-H. Yang, M. A. Brimble. Org. Lett.13, 5382 (2011).Search in Google Scholar
6 10.1039/b927219b, Z. E. Wilson, M. A. Brimble. Org. Biomol. Chem.8, 1284 (2010).Search in Google Scholar PubMed
7 10.1039/b800164m, Z. E. Wilson, M. A. Brimble. Nat. Prod. Rep.26, 44 (2009).Search in Google Scholar PubMed
8 10.1021/jo060018d, A. S. Stierle, D. B. Stierle, K. Kelly. J. Org. Chem.71, 5357 (2006).Search in Google Scholar PubMed
9a 10.1002/chem.201001133, T. N. Snaddon, P. Buchgraber, S. Schulthoff, C. Wirtz, R. Mynott, A. Fürstner. Chem.—Eur. J.16, 12133 (2010).Search in Google Scholar PubMed
9b 10.1002/anie.200803339, P. Buchgraber, T. N. Snaddon, C. Wirtz, R. Mynott, R. Goddard, A. Fürstner. Angew. Chem., Int. Ed.47, 8450 (2008).Search in Google Scholar PubMed
10a 10.1021/jo901221a, X. Wu, J. Zhou, B. B. Snider. J. Org. Chem.74, 6245 (2009).Search in Google Scholar
10b 10.1002/anie.200805488, X. Wu, J. Zhou, B. B. Snider. Angew. Chem., Int. Ed.48, 1283 (2009).Search in Google Scholar
11 10.1021/ja905387r, C. F. Bender, F. K. Yoshimoto, C. L. Paradise, J. K. De Brabander. J. Am. Chem. Soc.131, 11350 (2009).Search in Google Scholar
12 10.1021/ol102652t, T. A. Wenderski, M. A. Marsini, T. R. R. Pettus. Org. Lett.13, 118 (2011).Search in Google Scholar
13 10.1016/S0040-4020(01)85090-0, J. Chiarello, M. M. Jouillé. Tetrahedron44, 41 (1988).Search in Google Scholar
14 10.1021/ol0704338, J. Y. Zhou, B. B. Snider. Org. Lett.9, 2071 (2007).Search in Google Scholar
15 Isolation.Search in Google Scholar
15a 10.1007/BF00596449, H. Brockmann, K. H. Renneberg. Naturwissenschaften40, 59 (1953).Search in Google Scholar
15b 10.1007/BF00639946, H. Brockmann, K. H. Renneberg. Naturwissenschaften40, 166 (1953).Search in Google Scholar
15c 10.1016/S0040-4039(01)82822-7, H. Brockmann, W. Lenk, G. Schwantje, A. Zeeck. Tetrahedron Lett.7, 3525 (1966); Biological activity.Search in Google Scholar
15d M. E. Goldman, G. S. Salituro, J. A. Bowen, J. M. Williamson, D. L. Zink, W. A. Schleif, E. A. Emini. Mol. Pharmacol.38, 20 (1990).Search in Google Scholar
15e 10.1021/bi992661i, T. Ueno, H. Takahashi, M. Oda, M. Mizunuma, A. Yokoyama, Y. Goto, Y. Mizushina, K. Sakaguchi, H. Hayashi. Biochemistry39, 5995 (2000).Search in Google Scholar PubMed
16a C. Coronelli, H. Pagani, M. R. Bardone, G. C. Lancini. J. Antibiot.27, 161 (1974).Search in Google Scholar
16b 10.1016/S0040-4020(01)97439-3, M. R. Bardone, E. Martinelli, E. F. Zerilli, C. Coronelli. Tetrahedron30, 2747 (1974).Search in Google Scholar
17a M. Chino, K. Nishikawa, A. Yamada, M. Ohsono, T. Sawa, F. Hanaoka, M. Ishizuka, T. Takeuchi. J. Antibiot.51, 480 (1998).Search in Google Scholar
17b M. Chino, K. Nishikawa, M. Umekita, C. Hayashi, T. Yamazaki, T. Tsuchida, T. Sawa, M. Hamada, T. Takeuchi. J. Antibiot.49, 752 (1996).Search in Google Scholar
18 10.1002/ejoc.200601054, M. Brasholz, S. Sorgel, C. Azap, H. U. Reissig. Eur. J. Org. Chem. 3801 (2007).Search in Google Scholar
19 10.1002/1521-3773(20011217)40:24<4713::AID-ANIE4713>3.0.CO;2-N, T. Siu, D. H. Qin, S. J. Danishefsky. Angew. Chem., Int. Ed.40, 4713 (2001).Search in Google Scholar
20 10.1002/anie.200702382, S. Akai, K. Kakiguchi, Y. Nakamura, I. Kuriwaki, T. Dohi, S. Harada, O. Kubo, N. Morita, Y. Kita. Angew. Chem., Int. Ed.46, 7458 (2007).Search in Google Scholar
21a 10.1021/jo200398v, R. Bandichhor, A. N. Lowell, M. C. Kozlowski. J. Org. Chem.76, 6475 (2011).Search in Google Scholar
21b 10.1021/jo200399z, A. N. Lowell, M. W. Fennie, M. C. Kozlowski. J. Org. Chem.76, 6488 (2011).Search in Google Scholar
21c 10.1021/ol061112j, S. P. Waters, M. W. Fennie, M. C. Kozlowski. Org. Lett.8, 3243 (2006).Search in Google Scholar
22 C. Venkatesh, H. U. Reissig. Synthesis 3605 (2008).10.1055/s-0028-1083194Search in Google Scholar
23 10.1016/j.tet.2007.02.033, K. Y. Tsang, M. A. Brimble. Tetrahedron63, 6015 (2007).Search in Google Scholar
24 10.1039/p19910001433, D. L. J. Clive, A. Khodabocus, P. G. Vernon, A. G. Angoh, L. Bordeleau, D. S. Middleton, C. Lowe, D. Kellner. J. Chem. Soc., Perkin Trans. 1 1433 (1991).Search in Google Scholar
25 10.1021/ja1115524, K.-L. Wu, E. V. Mercado, T. R. R. Pettus. J. Am. Chem. Soc.133, 6114 (2011).Search in Google Scholar PubMed
26 10.1246/cl.2000.308, M. Namikoshi, H. Kobayashi, T. Yoshimoto, S. Meguro. Chem. Lett. 308 (2000).Search in Google Scholar
27 For reports on the synthesis of the spiro[chroman-2,1'(3'H)-isobenzofuran] core, see.Search in Google Scholar
27a 10.1071/CH9751145, J. W. Clark-Lewis, E. J. McGarry. Aust. J. Chem.28, 1145 (1975).Search in Google Scholar
27b 10.1021/ol8003244, M. A. Marsini, Y. D. Huang, C. C. Lindsey, K. L. Wu, T. R. R. Pettus. Org. Lett.10, 1477 (2008).Search in Google Scholar PubMed PubMed Central
27c M. Jay-Smith, D. P. Furkert, J. Sperry, M. A. Brimble. Synlett 1395 (2011).10.1055/s-0030-1260564Search in Google Scholar
28 10.1002/ejoc.200700583, G. Stavrakov, M. Keller, B. Breit. Eur. J. Org. Chem. 5726 (2007).Search in Google Scholar
29 CCDC 823856 contains the crystallographic data for this compound. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via <www.ccdc.cam.ac.uk/ data_request/cif>.Search in Google Scholar
30 10.1021/jo972247t, A. Couture, E. Deniau, P. Grandclaudon, C. Hoarau. J. Org. Chem.63, 3128 (1998).Search in Google Scholar
© 2013 Walter de Gruyter GmbH, Berlin/Boston
