The lactone concept: An efficient pathway to axially chiral natural products and useful reagents

Synthesis

Volumn , Issue 4, 1999, Pages 525-558

  Bringmann, Gerhard ^a   Breuning, Matthias ^a   Tasler, Stefan ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

Atropo divergent synthesis; Axial chirality; Biaryl ligands and reagents; Biaryl natural products; Lactone bridged biaryls

Indexed keywords

DIONCOPHYLLINE A; LACTONE; ORCINOL;

CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; CHIRALITY; CYCLIZATION; DIASTEREOISOMER; REACTION ANALYSIS; REVIEW; STEREOCHEMISTRY; STEREOSPECIFICITY; SYNTHESIS;

EID: 0032917881     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-3435     Document Type: Review

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178. Boyd, M. R.; Hallock, Y. F.; Cardellina II, J. H., Manfredi, K. P.; Blunt, J. W.; McMahon, J. B.; Buckheit Jr., R. W.; Bringmann, G.; Schäffer, M.; Cragg, G. M.; Thomas, D. W.; Jato, J. G. J. Med. Chem. 1994, 37, 1740.
179. Bringmann, G.; Harmsen, S.; Holenz, J.; Geuder, T.; Götz., R.; Keller, P. A.; Walter, R.; Hallock, Y. P.; Cardellina II, J. H.; Boyd, M. R. Tetrahedron 1994, 50, 9643.
180. Schlauer, J.; Ruckert, M.; Wiesen, B.; Herderich, M.; Aké Assi, L.; Haller, R. D.; Bär, S.; Fröhlich, K.-U.; Bringmann, G. Arch. Biochem. Biophys. 1998, 350, 87.
181. Bringmann, G.; Saeb, W.; François, G.; Schlauer, J. Pharm. Pharmacol. Lett. 1998, 8, 8.
182. For other synthetic approaches to michellamines, see references 143a, 144b and: (a) Kelly, T. R.; Garcia, A.; Lang, F.; Walsh, J. J.; Bhaskar, K. V.; Boyd, M. R.; Gotz, R.; Keller, P. A.; Walter, R.; Bringmann, G. Tetrahedron Lett. 1994, 35, 7621.
183. (b) Bringmann, G.; Götz, R.; Keller, P. A.; Walter, R.; Boyd, M, R.; Lang, F.; Garcia, A.; Walsh, J. J.; Tellitu, I.; Bhaskar, K. V.; Kelly, T. R. J. Org. Chem. 1998, 63, 1090.
184. G. Bringmann; In Phytopharmaka in Forschung and klinischer Anwendung; Rietbrock, N.; Loew, D., Ed.; Verlag Steinkopff: Darmstadt, 1995; p 113.
185. Bringmann, G.; Kinzinger, L. Photochemistry 1992, 31, 3297.
186. Bringmann, G.; Kinzinger, L.; Busse, H.; Zhao, C. Planta Med. 1992, 55 (Suppl. 1), 704.
187. Bringmann, G.; Kinzinger, L.; Ortmann, T.; de Souza, N. J. Phytochemistry 1994, 35, 259.
188. Bringmann, G.; Lisch, D.; Reuscher, H.; Aké Assi, L.; Günther, K. Phytochemistry 1991, 30, 1307.
189. Bringmann, G.; Pokorny, F.; Stablein, M.; Schäffer, M.; Aké Assi, L. Phytochemistry 1993, 33, 1511.
190. Bringmann, G.; Weirich, R.; Lisch, D.; Aké Assi, L. Planta Med. 1992, 58 (Suppl. 1), 703.
191. Anh, N. H.; Porzel, A.; Rippergcr, H.; Bringmann, G.; Schaffer, M.; God, R.; Sung, T. V.; Adam, G. Phytochemistry 1997, 45, 1287.
192. Bringmann, G.; Weirich, R.; Kinzinger, L.; Rübenacker, M.; unpublished results.
193. Bringmann, G.; Pabst, T.; Rycroft, D. S.; Connolly, J. D. Tetrahedron Lett. 1999, 40, 483.
194. Bringmann, G.; Pabst, T.; Busemann, S.; Peters, K.; Peters, E.-M. Tetrahedron 1998, 54, 1425.
195. Bringmann, G.; Pabst, T.; Hinrichs, J.; Rycroft, D. S.; Connolly, J. D.; unpublished results.
196. Bringmann, G.; Walter, R.; Ewers, C. L. J. Synlett 1991, 581.
197. Bringmann, G.; Hinrichs, J.; unpublished results.
198. Beecken, H.; Gottschalk, E.-M.; von Gizycki, U.; Krämer, H.; Maassen, D.; Matthies, H.-G.; Musso, H.; Rathjen, C.; Zahorszky, U.-I. Angew. Chem. 1961, 73, 665.
199. Lin, G.-Q.; Zhong, M. Tetrahedron Lett, 1996, 37, 3015.
200. Berhanu, E.; Fetene, M.; Dagne, E. Phytochemistry 1986, 25, 847.
201. Van Wyk, B.-E.; Yenesew, A.; Dagne, E. Biochem. Syst. Ecol. 1995, 23, 277.
202. Bringmann, G.; Kraus, J.; Menche, D.; Schlauer, J.; unpublished results.
203. Bringmann, G.; Menche, D.; Bezabih, M.; Abegaz, B, M.; Peters, K.; Peters, E.-M.; unpublished results.
204. Alexander, J.; Bhatia, A, V.; Mitscher, L. A.; Omoto, S.; Suzuki, T. J.Org. Chem. 1980, 45, 20.
205. (a) Noyori, R.; Kitamura, M. Angew. Chem. 1991, 103, 34; Angew. Chem., Int. Ed. Engl. 1991, 30, 49.
206. (a) Noyori, R.; Kitamura, M. Angew. Chem. 1991, 103, 34; Angew. Chem., Int. Ed. Engl. 1991, 30, 49.
207. (b) Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833.
208. Bringmann, G.; Breuning, M, Tetrahedron: Asymmetry 1998, 9, 667.
209. Bringmann, G.; Wuzik, A., Breuning, M.; unpublished results.
210. (a) Moberg, C. Angew. Chem. 1998, 110, 261; Angew. Chem., Int. Ed. Engl. 1998, 37, 248.
211. (a) Moberg, C. Angew. Chem. 1998, 110, 261; Angew. Chem., Int. Ed. Engl. 1998, 37, 248.
212. (b) Keyes, M. C.; Tolman, W, B. Adv. Cat. Proc. 1997, 2, 189.
213. Bringmann, G.; Breuning, M.; Vedder, C.; unpublished results.
214. Sec, i.a., the substitution of the O-functionality into an H-or P-substitutent in Schemes 36 and 52; for further transformations of C-and O-substitutents of biaryls into O-, N-H-, Br-, or I-and H-, C-, S-, or P-substitutents, respectively, sec: (a) Meyers, A. I.; Meier, A.; Rawson, D. J. Tetrahedron Lett. 1992, 33, 853.
215. (b) Wilson, J. M.; Cram, D. J. J. Org. Chem. 1984, 49, 4930.
216. (c) Brown, K. J.; Bery, M. S.; Murdoch, J. R. J. Org. Chem. 1985, 50, 4345.
217. (d) Uozumi, Y.; Suzuki, N.; Ogiwara, A.; Hayashi, T. Tetrahedron 1994, 50, 4293.
218. (e) Cai, D.; Payack, J. R; Bender, D. R.; Hughes, D. L.; Verhoeven, T. R.; Reider, P. J. J. Org. Chem. 1994, 59, 7180.
219. (f) Martorell, G.; Garcias, X.; Janura, M.; Saá, J. M. J. Org. Chem. 1998, 63, 3463 and references cited therein.
220. (g) Cossu, S.; De Lucchi, O.; Fabbri, D.; Valle, G.; Painter, G. F.; Smith, R. A. J. Tetrahedron 1997, 53, 6073.
221. (h) Kiyooka, S.-i.; Tsulsui, T.; Kira, T. Tetrahedron Lett. 1996, 37, 8903.
222. Rizzacasa, M. A. In Studies in Natural Product Chemistry, Vol. 20, Part F; Atta-ur-Rahman, Ed., Elsevier: Amsterdam, 1998; p 407.