Cross-coupling of highly pyramidalized alkenes: A straightforward access to functionalized tetrasecododecahedradienes

Organic Letters

Volumn 2, Issue 26, 2000, Pages 4225-4232

  Camps, Pelayo ^a   Pujol, Xavier ^a   Vázquez, Santiago ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000432870     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0067843     Document Type: Article

References (72)

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35. Relative stereochemistry was assigned by analogy with previous work (refs 8-10), in which structures were determined using a combination of NMR, synthetic, and X-ray crystallographic studies.
36. The detailed mechanism of the attack on the ring is under investigation but may be regarded as a six-electron electrocyclic ring closure.
37. The selectivity presumably arises from destabilisation by the p-OMe group of the alternative benzylic organolithium.
38. HH coupling constants between H-3 and H-3a. Unfortunately, the H-3a to H-7a coupling is not resolved.
39. We introduced the cumyl group as an alkyllithium-stable, acid-labile protecting group for our synthesis of (±)-kainic acid (ref 10). Snieckus has independently reported the use of the cumyl group in ortholithiation reactions: see Metallinos, C.; Nerdinger, S.; Snieckus, V. Org. Lett. 1999, 1, 1183.
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41. Ahmed, A.; Clayden, J. Unpublished results
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62. Crandall, J. K.; Ayers, T. A. J. Org. Chem. 1992, 57, 2993. Saito, S.; Shimada, K.; Yamamoto, H.; Martínez de Marigorta, E.; Fleming, I. J. Chem. Soc., Chem. Commun. 1997, 1299. Winemiller, M. D.; Harman, W. D. J. Org. Chem. 2000, 65, 1249. Hunter, R.; Richards, P. Tetrahedron Lett. 2000, 41, 3755. Kündig, E. P.; Ripa, A.; Bernardinelli, G. Angew. Chem., Int. Ed. Engl. 1992, 31, 1071. Padwa, A.; Filipkowski, M. A.; Kline, D. N.; Murphree, S. S.; Yeske, P. E. J. Org. Chem. 1993, 58, 2061. Pearson, A. J.; Gontcharov, A. V.; Zhu, P. Y. Tetrahedron 1997, 53, 3849. Brown, D. W.; Lindquist, M.; Mahon, M. F.; Malm, B.; Nilsson, G. N.; Ninan, A.; Sainsbury, M.; Westerlund, C. J. Chem. Soc., Perkin Trans. 1 1997, 2337. Maruoka, K.; Ito, M.; Yamamoto, H. J. Am. Chem. Soc. 1995, 117, 9091. Saito, S.; Sone, T.; Shimada, K.; Yamamoto, H. Synlett 1999, 81.
63. Crandall, J. K.; Ayers, T. A. J. Org. Chem. 1992, 57, 2993. Saito, S.; Shimada, K.; Yamamoto, H.; Martínez de Marigorta, E.; Fleming, I. J. Chem. Soc., Chem. Commun. 1997, 1299. Winemiller, M. D.; Harman, W. D. J. Org. Chem. 2000, 65, 1249. Hunter, R.; Richards, P. Tetrahedron Lett. 2000, 41, 3755. Kündig, E. P.; Ripa, A.; Bernardinelli, G. Angew. Chem., Int. Ed. Engl. 1992, 31, 1071. Padwa, A.; Filipkowski, M. A.; Kline, D. N.; Murphree, S. S.; Yeske, P. E. J. Org. Chem. 1993, 58, 2061. Pearson, A. J.; Gontcharov, A. V.; Zhu, P. Y. Tetrahedron 1997, 53, 3849. Brown, D. W.; Lindquist, M.; Mahon, M. F.; Malm, B.; Nilsson, G. N.; Ninan, A.; Sainsbury, M.; Westerlund, C. J. Chem. Soc., Perkin Trans. 1 1997, 2337. Maruoka, K.; Ito, M.; Yamamoto, H. J. Am. Chem. Soc. 1995, 117, 9091. Saito, S.; Sone, T.; Shimada, K.; Yamamoto, H. Synlett 1999, 81.
64. Crandall, J. K.; Ayers, T. A. J. Org. Chem. 1992, 57, 2993. Saito, S.; Shimada, K.; Yamamoto, H.; Martínez de Marigorta, E.; Fleming, I. J. Chem. Soc., Chem. Commun. 1997, 1299. Winemiller, M. D.; Harman, W. D. J. Org. Chem. 2000, 65, 1249. Hunter, R.; Richards, P. Tetrahedron Lett. 2000, 41, 3755. Kündig, E. P.; Ripa, A.; Bernardinelli, G. Angew. Chem., Int. Ed. Engl. 1992, 31, 1071. Padwa, A.; Filipkowski, M. A.; Kline, D. N.; Murphree, S. S.; Yeske, P. E. J. Org. Chem. 1993, 58, 2061. Pearson, A. J.; Gontcharov, A. V.; Zhu, P. Y. Tetrahedron 1997, 53, 3849. Brown, D. W.; Lindquist, M.; Mahon, M. F.; Malm, B.; Nilsson, G. N.; Ninan, A.; Sainsbury, M.; Westerlund, C. J. Chem. Soc., Perkin Trans. 1 1997, 2337. Maruoka, K.; Ito, M.; Yamamoto, H. J. Am. Chem. Soc. 1995, 117, 9091. Saito, S.; Sone, T.; Shimada, K.; Yamamoto, H. Synlett 1999, 81.
65. Crandall, J. K.; Ayers, T. A. J. Org. Chem. 1992, 57, 2993. Saito, S.; Shimada, K.; Yamamoto, H.; Martínez de Marigorta, E.; Fleming, I. J. Chem. Soc., Chem. Commun. 1997, 1299. Winemiller, M. D.; Harman, W. D. J. Org. Chem. 2000, 65, 1249. Hunter, R.; Richards, P. Tetrahedron Lett. 2000, 41, 3755. Kündig, E. P.; Ripa, A.; Bernardinelli, G. Angew. Chem., Int. Ed. Engl. 1992, 31, 1071. Padwa, A.; Filipkowski, M. A.; Kline, D. N.; Murphree, S. S.; Yeske, P. E. J. Org. Chem. 1993, 58, 2061. Pearson, A. J.; Gontcharov, A. V.; Zhu, P. Y. Tetrahedron 1997, 53, 3849. Brown, D. W.; Lindquist, M.; Mahon, M. F.; Malm, B.; Nilsson, G. N.; Ninan, A.; Sainsbury, M.; Westerlund, C. J. Chem. Soc., Perkin Trans. 1 1997, 2337. Maruoka, K.; Ito, M.; Yamamoto, H. J. Am. Chem. Soc. 1995, 117, 9091. Saito, S.; Sone, T.; Shimada, K.; Yamamoto, H. Synlett 1999, 81.
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