Beilstein J. Org. Chem. 2015, 11, 1700–1706.
14.Ishii, H.; Murakami, Y. Tetrahedron 1975, 31, 933–938.
The antimicrobial activity of synthetic indiacen B (2) was in the
same range as that originally determined for the isolated natural
product.
15.Somei, M. Chem. Pharm. Bull. 1986, 34, 4109–4115.
16.Benhida, R.; Lecubin, F.; Fourrey, J.-L.; Castellanos, L. R.; Quintero, L.
Tetrahedron Lett. 1999, 40, 5701–5703.
Supporting Information
17.Falck, J. R.; Patel, P. K.; Bandyopadhyay, A. J. Am. Chem. Soc. 2007,
Supporting Information File 1
Experimental procedures, bioactivity tables, X-ray figures
and tables, HPLC chromatograms and NMR spectra for all
compounds, NOESY analyses.
18.Goli, M.; He, A.; Falck, J. R. Org. Lett. 2011, 13, 344–346.
19.Murase, M.; Watanabe, K.; Kurihara, T.; Tobinaga, S.
20.Sagadevan, A.; Hwang, K. C. Adv. Synth. Catal. 2012, 354,
21.Kanemesa, S.; Yamamoto, H.; Kobayashi, S. Tetrahedron Lett. 1996,
22.Jong, S.-J.; Chen, C.-T.; Fang, J.-M.; Liu, Y.-H.; Lee, G.-H.; Wang, Y.
C. R. Acad. Sci., Ser. IIc: Chim. 2001, 4, 487–496.
Acknowledgements
We thank Merck KGaA (Darmstadt, Germany) for chromatog-
raphy materials. BASF Group (Ludwigshafen, Germany) and
Honeywell Specialty Chemicals Seelze GmbH (Seelze,
Germany) are thanked for the donation of solvents. Tina
Bohlmann is thanked for the synthesis of tricyclic cyclopen-
tanones 17 and 18. Wera Collisi, Helmholtz Center for Infec-
tion Research, Department Microbial Drugs, is thanked for
biotests of indiacen B.
23.Zhou, L.; Zhang, Y. Synth. Commun. 2000, 30, 597–607.
24.Cabrera, A.; Le Lagadec, R.; Sharma, P.; Arias, J. L.; Toscano, R. A.;
Velasco, L.; Gaviño, R.; Alvarez, C.; Salmón, V.
J. Chem. Soc., Perkin Trans. 1 1998, 3609–3618.
25.Shinohara, I.; Okue, M.; Yamada, Y.; Nagaoka, H. Tetrahedron Lett.
26.Jong, S.-J.; Fang, J.-M. Org. Lett. 2000, 2, 1947–1949.
References
1. Vougogiannopoulou, K.; Fokialakis, N.; Aligiannis, N.; Cantrell, C.;
Skaltsounis, A.-L. Org. Lett. 2010, 12, 1908–1911.
27.Evans, W. J.; Brady, J. C.; Ziller, J. W. Inorg. Chem. 2002, 41,
28.Zhu, X.; Wang, S.; Zhou, S.; Wei, Y.; Zhang, L.; Wang, F.; Feng, Z.;
Guo, L.; Mu, X. Inorg. Chem. 2012, 51, 7134–7143.
2. Vougogiannopoulou, K.; Fokialakis, N.; Aligiannis, N.; Cantrell, C.;
Skaltsounis, A.-L. Planta Med. 2011, 77, 1559–1561.
29.Blot, V.; Reissig, H.-U. Synlett 2006, 2763–2766.
3. Moreira, V. F.; Oliveira, R. R.; Mathias, L.; Braz-Filho, R.;
Curcino Vieira, I. J. Helv. Chim. Acta 2010, 93, 1751–1757.
30.Beemelmanns, C.; Gross, S.; Reissig, H.-U. Chem. – Eur. J. 2013, 19,
5. Steinmetz, H.; Mohr, K. I.; Zander, W.; Jansen, R.; Gerth, K.; Müller, R.
6. Jansen, R.; Mohr, K. I.; Bemecker, S.; Stadler, M.; Müller, R.
7. Nwaji, M. N.; Onyiriuka, S. O.; Taylor, D. A. H.
J. Chem. Soc., Chem. Commun. 1972, 327.
31.Nicolaou, K. C.; Ellery, S. P.; Chen, J. S. Angew. Chem., Int. Ed. 2009,
Angew. Chem. 2009, 121, 7276–7301.
32.Szostak, M.; Procter, D. J. Angew. Chem., Int. Ed. 2012, 51,
Angew. Chem. 2012, 124, 9372–9390.
33.Jacubert, M.; Provot, O.; Peyrat, J.-F.; Hamze, A.; Brion, J.-D.;
Alami, M. Tetrahedron 2010, 66, 3775–3787.
8. Lindel, T.; Bräuchle, L.; Golz, G.; Böhrer, P. Org. Lett. 2007, 9,
34.Kern, J. C.; Terefenko, E.; Trybulski, E.; Berrodin, T. J.; Cohen, J.;
Winneker, R. C.; Yudt, M. R.; Zhang, Z.; Zhu, Y.; Zhang, P.
Bioorg. Med. Chem. Lett. 2009, 19, 6666–6669.
9. Adla, S. K.; Golz, G.; Jones, P. G.; Lindel, T. Synthesis 2010,
10.Adla, S. K.; Sasse, F.; Kelter, G.; Fiebig, H.-H.; Lindel, T.
11.Lindel, T.; Marsch, N.; Adla, S. K. Top. Curr. Chem. 2012, 309,
35.Moyer, M. P.; Shiurba, J. F.; Rapoport, H. J. Org. Chem. 1986, 51,
36.Nakatsuji, H.; Morimoto, M.; Misaki, T.; Tanabe, Y. Tetrahedron 2007,
37.Semmelhack, M. F.; Knochel, P.; Singleton, T. Tetrahedron Lett. 1993,
38.Wang, Q.; Deredas, D.; Huyhn, C.; Schlosser, M. Chem. – Eur. J.
12.Nkunya, M. H. H.; Makangara, J. J.; Jonker, S. A. Nat. Prod. Res.
13.Ishii, H.; Murakami, Y.; Furuse, T.; Takeda, H.; Ikeda, N.
Tetrahedron Lett. 1973, 14, 355–358.
1705