An approach toward the triquinane-type skeleton via reagent-controlled skeletal rearrangements. A facile method for protection-deprotection of organomercurials, tuning the selectivity of Wagner-Meerwein migrations, and a new route to annulated lactones

Journal of Organic Chemistry

Volumn 64, Issue 1, 1999, Pages 101-119

  Kočovský, Pavel ^a   Dunn, Victoria ^a   Gogoll, Adolf ^b   Langer, Vratislav ^c  

^a UNIVERSITY OF LEICESTER   (United Kingdom)

^b UPPSALA UNIVERSITY   (Sweden)

^c CHALMERS UNIVERSITY OF TECHNOLOGY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; CYCLOPROPANE; LACTONE; ORGANOMERCURY COMPOUND; PALLADIUM; TRIQUINANE; UNCLASSIFIED DRUG;

AEROBIC METABOLISM; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; METHODOLOGY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0344334078     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9812882     Document Type: Article

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169. 11
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198. (c) Grennberg, H.; Bäckvall, J.-E. Chem.-Eur. J. 1998, 4, 1083.
199. (a) Larock, R. C.; Hightower, T. R. J. Org. Chem. 1993, 58, 5298.
200. 2, see:
201. (c) Andersson, P. G.; Bäckvall, J.-E. J. Am. Chem. Soc. 1992, 114, 8696.
202. 2+ reagents.
203. 3 ↔ 19-H and 4aα-H ↔ 7β-H have been identified.
204. A similar retardation effect was observed for the Hg(II)-mediated cyclopropane cleavage in the methyl ether 4 as compared to alcohol 3 (vide supra).
205. Thallium(III) nitrate gave an intractable mixture of a number of products.
206. Hydrogenolysis, as an alternative mechanism, seems unlikely in the oxidative medium.
207. Saunders, M.; Chandrasekhar, J.; Schleyer, P. v. R. Rearrangements of Carbocations. In Rearrangements in Ground and Excited States; de Mayo, P., Ed.; Academic: New York, 1980; Vol. 1, p 24.
208. 2HgCl group in 49c: if the reaction proceeded via C, the latter configuratuion would have to be α. Conformation D appears to be most congested so that its attack by the electrophile is unlikely.
209. Alternatively, if the attack occurred on the Si-face of the double bond in the conformation B (a less likely scenario), syn migration (rather than the usual anti) would have to follow in order to give the observed product. However, a clockwise rotation of the coordinated vinyl group prior to the Wagner-Meerwein migration would lead to the conformation A (Si), which would then trigger the migration of C(5).-
210. Finn, M. G.; Sharpless, K. B. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic: New York, 1985; Vol. 5, p 159.
211. (a) Stork, G.; Kahne, D. E. J. Am. Chem. Soc. 1983, 105, 1072.
212. (b) Crabtree, R. H.; Davis, M. W. Organometallics 1983, 2, 681.
213. (c) Crabtree, R. H.; Davis, M. W. J. Org. Chem. 1986, 51, 2655.
214. (d) Burk, M. J.; McGrath, M. P.; Wheeler, R.; Crabtree, R. H. J. Am. Chem. Soc. 1988, 110, 5034.
215. (e) Watanabe, Y.; Mizuhara, Y.; Shiota, M. J. Org. Chem. 1966, 31, 3785.
216. Garrett, C. E.; Fu, G. C. J. Org. Chem. 1998, 63, 1370.
217. For reviews on steering the reagent/catalyst by a neighboring group, see: (a) Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307.
218. (b) Brown, J. M. Angew. Chem., Int Ed. Engl. 1987, 26, 190.
219. (a) Bose, A. K.; Krishnan, L.; Wagle, D. R.; Manhas, M. S. Tetrahedron Lett. 1988, 27, 5955.
220. (b) Alonso, R. A.; Burgey, C. S.; Rao, B. V.; Vite, C. D.; Vollerthun, R.; Zottola, M. A.; Fraser-Reid, B. J. Am. Chem. Soc. 1993, 115, 6666.
221. (c) Hamed, O.; Henry, P. M. Organometallics 1997, 16, 4903.
222. (d) Hamed, O.; Thompson, C.; Henry, P. M. J. Org. Chem. 1997, 62, 7082.
223. (e) Pellisier, H.; Michellys, P.-Y.; Santelli, M. Tetrahedron 1997, 53, 10733.
224. (f) Nemoto, H.; Miyata, J.; Yoshida, M.; Raku, N.; Fukumoto, K. J. Org. Chem. 1997, 62, 7850.
225. For theoretical approach, see: (a) Siegbahn, P. E. M. J. Am. Chem. Soc. 1995, 117, 5409.
226. (b) Strömberg, S.; Svensson, M.; Zetterberg, K. Organometallics 1997, 16, 3165.
227. Note that the MeO group is unlikely to assume a different conformation by rotating about the MeO-C(6) bond and, at the same time, offer one of the electron pairs to coordination, as this would impose a clash with the angular methyl.
228. 3 but contains an additional angular methyl at position corresponding to 3α in 43, exhibited high preference for pathway α, which further demonstrates the importance of conformational effects.
229. For the Pd(0)-catalyzed method, see: (a) Henin, F.; Pete, J.-P. Tetrahedron Lett. 1983, 24, 4687.
230. (b) Henin, F.; Muzart, J.; Pete, J.-P. Tetrahedron Lett. 1986, 27, 6332. For Ni-catalyzed carbonylation, see:
231. (c) Semmelhack, M. F.; Brickener, J. S. J. Org. Chem. 1981, 46, 1723 and refs cited therein. Other methods make use of Pd-catalyzed carbonylation of acetylenic alcohols:
232. (d) Chaudarian, C. G.; Woo, S. L.; Clark, R. D.; Heathcock, C. H. Tetrahedron Lett. 1976, 1769.
233. (e) Murray, T. F.; Norton, J. R. J. Am. Chem. Soc. 1979, 101, 4107 and refs cited therein.
234. 94
235. 33 See also: Kočovský, P.; Grech, J. M.; Mitchell, W. L. Tetrahedron Lett. 1996, 37, 1125.
236. For the notation, see: Kočovský, P.; Stieborová, I. J. Chem. Soc., Perkin Trans. 1 1987, 1969.
237. Johnson, C. K. Technical Report ORNL-5138; Oak Ridge National Laboratory: Oak Ridge, TN, 1976.