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Volumn 63, Issue 12, 2010, Pages 1665-1678

The Pd-catalyzed Alder-ene reactions of N-protected and propargylated 1-amino-2-aryl-2-cyclohexenes as a new route to C3a-arylhexahydroindoles: Towards the total synthesis of tazettine

(3) Lehmann, Anna L a Willis, Anthony C a Banwell, Martin G a

a AUSTRALIAN NATIONAL UNIVERSITY (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

ALDER-ENE REACTION; CYCLOHEXENES; INTRAMOLECULAR ALDER-ENE REACTION; PALLADIUM ACETATE; TOTAL SYNTHESIS;

ORGANOMETALLICS; SYNTHESIS (CHEMICAL);

PALLADIUM;

EID: 78650114488 PISSN: 00049425 EISSN: None Source Type: Journal
DOI: 10.1071/CH10359 Document Type: Conference Paper

Times cited : (22)

References (45)

1
- 62049084653
- references cited therein, doi:10.1016/J. TET.2008.10.048
- E. A. Ilardi, M. J. Isaacman, Y.-c. Qin, S. A. Shelly, A. Zakarian, Tetrahedron 2009, 65, 3261 and references cited therein. doi:10.1016/J. TET.2008.10.048
- (2009) Tetrahedron. , vol.65 , pp. 3261
- Ilardi, E.A.¹ Isaacman, M.J.² Qin, Y.-.³ Shelly, S.A.⁴ Zakarian, A.⁵

2
- 1642343936
- Palladium-Catalyzed Asymmetric Allylic Substitution of 2-Arylcyclohexenol Derivatives: Asymmetric Total Syntheses of (+)-Crinamine, (-)-Haemanthidine, and (+)-Pretazettine
- DOI 10.1021/jo030309b
- See, for example, (a) T. Nishimata, Y. Sato, M. Mori, J. Org. Chem. 2004, 69, 1837. doi:10.1021/JO030309B (Pubitemid 38366646)
- (2004) Journal of Organic Chemistry , vol.69 , Issue.6 , pp. 1837-1843
- Nishimata, T.¹ Sato, Y.² Mori, M.³

3
- 33747780396
- doi:10.1016/J. TET.2006.07.027
- (b) F.-M. Zhang, Y.-Q. Tu, J.-D. Liu, X.-H. Fan, L. Shi, X.-D. Hu, S.-H. Wang, Y.-Q. Zhang, Tetrahedron 2006, 62, 9446. doi:10.1016/J. TET.2006.07.027
- (2006) Tetrahedron. , vol.62 , pp. 9446
- Zhang, F.-M.¹ Tu, Y.-Q.² Liu, J.-D.³ Fan, X.-H.⁴ Shi, L.⁵ Hu, X.-D.⁶ Wang, S.-H.⁷ Zhang, Y.-Q.⁸

4
- 33747013332
- doi:10.1016/J. TET.2006.07.005
- (c) C. Bru, C. Guillou, Tetrahedron 2006, 62, 9043. doi:10.1016/J. TET.2006.07.005
- (2006) Tetrahedron. , vol.62 , pp. 9043
- Bru, C.¹ Guillou, C.²

5
- 50149083686
- doi:10.1021/JO8008353
- (d) N. T. Tam, J. Chang, E.-J. Jung, C.-G. Cho, J. Org. Chem. 2008, 73, 6258. doi:10.1021/JO8008353
- (2008) J. Org. Chem. , vol.73 , pp. 6258
- Tam, N.T.¹ Chang, J.² Jung, E.-J.³ Cho, C.-G.⁴

6
- 72049125857
- (e) J.-D. Liu, S.-H. Wang, F.-M. Zhang, Y.-Q. Tu, Y.-Q. Zhang, Synlett 2009, 3040.
- (2009) Synlett , pp. 3040
- Liu, J.-D.¹ Wang, S.-H.² Zhang, F.-M.³ Tu, Y.-Q.⁴ Zhang, Y.-Q.⁵

7
- 67650296165
- doi:10.1021/OL901230W
- (f) A. D. Findlay, M. G. Banwell, Org. Lett. 2009, 11, 3160. doi:10.1021/OL901230W
- (2009) Org. Lett. , vol.11 , pp. 3160
- Findlay, A.D.¹ Banwell, M.G.²

8
- 0032557235
- Total synthesis of (±)-tazettine
- DOI 10.1021/ja974317j
- See, for example, (a) J. H. Rigby, A. Cavezza, M. J. Heeg, J. Am. Chem. Soc. 1998, 120, 3664. doi:10.1021/JA974317J (Pubitemid 28218442)
- (1998) Journal of the American Chemical Society , vol.120 , Issue.15 , pp. 3664-3670
- Rigby, J.H.¹ Cavezza, A.² Heeg, M.J.³

9
- 0034719244
- doi:10.1021/OL9911472
- (b) S. W. Baldwin, J. S. Debenham, Org. Lett. 2000, 2, 99. doi:10.1021/OL9911472
- (2000) Org. Lett. , vol.2 , pp. 99
- Baldwin, S.W.¹ Debenham, J.S.²

10
- 0027289151
- See, for example, a, doi:10.1021/JO00061A005
- See, for example, (a) H. Ishibashi, N. Uemura, H. Nakatani, M. Okazaki, T. Sato, N. Nakamura, M. Ikeda, J. Org. Chem. 1993, 58, 2360. doi:10.1021/JO00061A005
- (1993) J. Org. Chem. , vol.58 , pp. 2360
- Ishibashi, H.¹ Uemura, N.² Nakatani, H.³ Okazaki, M.⁴ Sato, T.⁵ Nakamura, N.⁶ Ikeda, M.⁷

11
- 0001092327
- doi:10.1021/JO9815249
- (b) T. Nishimata, M. Mori, J. Org. Chem. 1998, 63, 7586. doi:10.1021/JO9815249
- (1998) J. Org. Chem. , vol.63 , pp. 7586
- Nishimata, T.¹ Mori, M.²

12
- 0033601284
- Synthetic studies of cis-3a-aryloctahydroindole derivatives by copper- catalyzed cyclization of N-allyltrichloroacetamides: Facile construction of benzylic quaternary carbons by carbon-carbon bond-forming reactions
- DOI 10.1021/jo9912146
- (c) S.-I. Iwamatsu, K. Matsubara, H. Nagashima, J. Org. Chem. 1999, 64, 9625. doi:10.1021/JO9912146 (Pubitemid 30027304)
- (1999) Journal of Organic Chemistry , vol.64 , Issue.26 , pp. 9625-9631
- Iwamatsu, S.-I.¹ Matsubara, K.² Nagashima, H.³

13
- 0035804964
- Application of furanyl carbamate cycloadditions toward the synthesis of hexahydroindolinone alkaloids
- DOI 10.1021/jo010020z
- (d) A. Padwa, M. A. Brodney, M. Dimitroff, B. Liu, T. Wu, J. Org. Chem. 2001, 66, 3119 and references cited therein. doi:10.1021/JO010020Z (Pubitemid 32879754)
- (2001) Journal of Organic Chemistry , vol.66 , Issue.9 , pp. 3119-3128
- Padwa, A.¹ Brodney, M.A.² Dimitroff, M.³ Liu, B.⁴ Wu, T.⁵

14
- 68149142567
- See, for example, a, doi:10.1021/OL901364N
- See, for example, (a) M. T. Jones, B. D. Schwartz, A. C. Willis, M. G. Banwell, Org. Lett. 2009, 11, 3506. doi:10.1021/OL901364N
- (2009) Org. Lett. , vol.11 , pp. 3506
- Jones, M.T.¹ Schwartz, B.D.² Willis, A.C.³ Banwell, M.G.⁴

15
- 77957701536
- doi:10.1071/CH10201
- (b) M. G. Banwell, X. Ma, O. P. Karunaratne, A. C. Willis, Aust. J. Chem. 2010, 63, 1437. doi:10.1071/CH10201
- (2010) Aust. J. Chem. , vol.63 , pp. 1437
- Banwell, M.G.¹ Ma, X.² Karunaratne, O.P.³ Willis, A.C.⁴

16
- 50549206141
- structure elucidation, doi:10.1016/S0040-4039 01 93306-4
- (a) C. F. Murphy, W. C. Wildman, Tetrahedron Lett. 1964, 5, 3857 (structure elucidation). doi:10.1016/S0040-4039 (01) 93306-4
- (1964) Tetrahedron. Lett. , vol.5 , pp. 3857
- Murphy, C.F.¹ Wildman, W.C.²

17
- 1642318908
- synthesis, doi:10.1016/S0040-4039 00 78769-7
- (b) K. Isobe, J. Taga, Y. Tsuda, Tetrahedron Lett. 1976, 17, 2331 (synthesis). doi:10.1016/S0040-4039 (00) 78769-7
- (1976) Tetrahedron. Lett. , vol.17 , pp. 2331
- Isobe, K.¹ Taga, J.² Tsuda, Y.³

18
- 0024787079
- doi:10.1039/C39890001767
- (a) H. Ishibashi, H. Nakatani, S. Iwami, T. Sato, N. Nakamura, M. Ikeda, J. Chem. Soc. Chem. Commun. 1989, 1767. doi:10.1039/C39890001767
- (1989) J. Chem. Soc. Chem. Commun. , pp. 1767
- Ishibashi, H.¹ Nakatani, H.² Iwami, S.³ Sato, T.⁴ Nakamura, N.⁵ Ikeda, M.⁶

19
- 0001646515
- doi:10.1021/JO00023A019
- (b) S. W. Baldwin, J. Aubé, A. T. McPhail, J. Org. Chem. 1991, 56, 6546. doi:10.1021/JO00023A019
- (1991) J. Org. Chem. , vol.56 , pp. 6546
- Baldwin, S.W.¹ Aubé, J.² McPhail, A.T.³

20
- 0002524474
- For useful descriptions of the Alder-ene reaction, including metalcatalyzed processes, see: a, doi:10.1021/AR00170A004
- For useful descriptions of the Alder-ene reaction, including metalcatalyzed processes, see: (a) B. M. Trost, Acc. Chem. Res. 1990, 23, 34. doi:10.1021/AR00170A004
- (1990) Acc. Chem. Res. , vol.23 , pp. 34
- Trost, B.M.¹

21
- 33748241769
- doi:10.1002/ANIE.199606621
- (b) A. Goeke, M. Sawamura, R. Kuwano, Y. Ito, Angew. Chem. Int. Ed. Engl. 1996, 35, 662. doi:10.1002/ANIE.199606621
- (1996) Angew. Chem. Int. Ed. Engl. , vol.35 , pp. 662
- Goeke, A.¹ Sawamura, M.² Kuwano, R.³ Ito, Y.⁴

22
- 0037125488
- Highly enantioselective syntheses of functionalized α-methylene- γ-butyrolactones via Rh(I)-catalyzed intramolecular Alder ene reaction: Application to formal synthesis of (+)-pilocarpine
- DOI 10.1021/ja020052j
- (c) A. Lei, M. He, X. Zhang, J. Am. Chem. Soc. 2002, 124, 8198. doi:10.1021/JA020052J (Pubitemid 34875376)
- (2002) Journal of the American Chemical Society , vol.124 , Issue.28 , pp. 8198-8199
- Lei, A.¹ He, M.² Zhang, X.³

23
- 32344433949
- Elsevier Academic Press: Burlington, MA and references cited therein
- (d) L. Kürti, B. Czakó, Strategic Applications of Named Reactions in Organic Synthesis 2005, pp. 6-7 (Elsevier Academic Press: Burlington, MA) and references cited therein.
- (2005) Strategic Applications of Named Reactions in Organic Synthesis , pp. 6-7
- Kürti, L.¹ Czakó, B.²

24
- 24644487836
- Pyrroles and gem-dihalocyclopropanes as building blocks for alkaloid synthesis
- DOI 10.2174/138527205774370469
- M. G. Banwell, D. A. S. Beck, P. C. Stanislawski, M. O. Sydnes, R. M. Taylor, Curr. Org. Chem. 2005, 9, 1589 and references cited therein. doi:10.2174/138527205774370469 (Pubitemid 41264302)
- (2005) Current Organic Chemistry , vol.9 , Issue.15 , pp. 1589-1600
- Banwell, M.G.¹ Beck, D.A.S.² Stanislawski, P.C.³ Sydnes, M.O.⁴ Taylor, R.M.⁵

25
- 0000983917
- doi:10.1071/CH9942235
- (a) M. G. Banwell, C. J. Cowden, Aust. J. Chem. 1994, 47, 2235. doi:10.1071/CH9942235
- (1994) Aust. J. Chem. , vol.47 , pp. 2235
- Banwell, M.G.¹ Cowden, C.J.²

26
- 0004992299
- doi:10.1039/P19940003515
- (b) M. G. Banwell, C. J. Cowden, R. W. Gable, J. Chem. Soc., Perkin Trans. 1 1994, 3515. doi:10.1039/P19940003515
- (1994) J. Chem. Soc., Perkin Trans. 1 , pp. 3515
- Banwell, M.G.¹ Cowden, C.J.² Gable, R.W.³

27
- 34247505524
- Equilibrium vs ground-state planarity of the CONH linkage
- DOI 10.1021/jp067278j
- J. Demaison, A. G. Császár, I. Kleiner, H. Møllendal, J. Phys. Chem. A 2007, 111, 2574. doi:10.1021/JP067278J (Pubitemid 46652726)
- (2007) Journal of Physical Chemistry A , vol.111 , Issue.13 , pp. 2574-2586
- Demaison, J.¹ Csaszar, A.G.² Kleiner, I.³ Mollendal, H.⁴

28
- 0030852154
- Flexible and convergent total synthesis of cyclotheonamide B
- DOI 10.1021/jo961447m
- (a) H. M. M. Bastiaans, J. L. van der Baan, H. C. J. Ottenheijm, J. Org. Chem. 1997, 62, 3880 and references cited therein. doi:10.1021/JO961447M (Pubitemid 27296163)
- (1997) Journal of Organic Chemistry , vol.62 , Issue.12 , pp. 3880-3889
- Bastiaans, H.M.M.¹ Van Der Baan, J.L.² Ottenheijm, H.C.J.³

29
- 0032497661
- doi:10.1016/S0040-4039 98 01631-1
- (b) A. J. Zhang, D. H. Russell, J. Zhu, K. Burgess, Tetrahedron Lett. 1998, 39, 7439. doi:10.1016/S0040-4039 (98) 01631-1
- (1998) Tetrahedron. Lett. , vol.39 , pp. 7439
- Zhang, A.J.¹ Russell, D.H.² Zhu, J.³ Burgess, K.⁴

30
- 37049074651
- doi:10.1039/P29860000787
- (a) R. L. Beddoes, L. Dalton, J. A. Joule, O. S. Mills, J. D. Street, C. I. F. Watt, J. Chem. Soc., Perkin Trans. 2 1986, 787. doi:10.1039/P29860000787
- (1986) J. Chem. Soc., Perkin Trans. 2 , pp. 787
- Beddoes, R.L.¹ Dalton, L.² Joule, J.A.³ Mills, O.S.⁴ Street, J.D.⁵ Watt, C.I.F.⁶

31
- 0008806065
- references cited therein, doi:10.1016/0166-1280 92 87168-Y
- (b) M. C. Menziani, M. Cocchi, P. G. De Benedetti, J. Mol. Struct. THEOCHEM 1992, 256, 217 and references cited therein. doi:10.1016/0166-1280 (92) 87168-Y
- (1992) J. Mol. Struct. THEOCHEM , vol.256 , pp. 217
- Menziani, M.C.¹ Cocchi, M.² De Benedetti, P.G.³

32
- 0029915116
- doi:10.1016/0040-4020 96 00096-8
- (c) J. Cobb, I. N. Demetropoulos, D. Korakas, S. Skoulika, G. Varvounis, Tetrahedron 1996, 52, 4485. doi:10.1016/0040-4020 (96) 00096-8
- (1996) Tetrahedron. , vol.52 , pp. 4485
- Cobb, J.¹ Demetropoulos, I.N.² Korakas, D.³ Skoulika, S.⁴ Varvounis, G.⁵

33
- 0033016157
- doi:10.1039/A809533G
- (d) Y. Zhao, M. Helliwell, J. A. Joule, J. Chem. Res. (S) 1999, 312. doi:10.1039/A809533G
- (1999) J. Chem. Res. (S) , pp. 312
- Zhao, Y.¹ Helliwell, M.² Joule, J.A.³

34
- 0029119899
- doi:10.1016/0040-4039 95 01316-A
- T. Fukuyama, C.-K. Jow, M. Cheung, Tetrahedron Lett. 1995, 36, 6373. doi:10.1016/0040-4039 (95) 01316-A
- (1995) Tetrahedron. Lett. , vol.36 , pp. 6373
- Fukuyama, T.¹ Jow, C.-K.² Cheung, M.³

35
- 84947151032
- doi:10.1080/00397918108063618
- N. Miyaura, T. Yanagi, A. Suzuki, Synth. Commun. 1981, 11, 513. doi:10.1080/00397918108063618
- (1981) Synth. Commun. , vol.11 , pp. 513
- Miyaura, N.¹ Yanagi, T.² Suzuki, A.³

36
- 33750309481
- Concise assembly of the polycyclic frameworks associated with the hapalindole and fischerindole alkaloids
- DOI 10.1021/ol062020x
- M. G. Banwell, X. Ma, R. M. Taylor, A. C. Willis, Org. Lett. 2006, 8, 4959. doi:10.1021/OL062020X (Pubitemid 44629503)
- (2006) Organic Letters , vol.8 , Issue.21 , pp. 4959-4961
- Banwell, M.G.¹ Ma, X.² Taylor, R.M.³ Willis, A.C.⁴

37
- 0035861034
- Tandem catalysis: The sequential mediation of olefin metathesis, hydrogenation, and hydrogen transfer with single-component Ru complexes
- DOI 10.1021/ja016431e
- J. Louie, C. W. Bielawski, R. H. Grubbs, J. Am. Chem. Soc. 2001, 123, 11312. doi:10.1021/JA016431E (Pubitemid 33065377)
- (2001) Journal of the American Chemical Society , vol.123 , Issue.45 , pp. 11312-11313
- Louie, J.¹ Bielawski, C.W.² Grubbs, R.H.³

38
- 0013399907
- Ed. J.-L. Luche Plenum Press: New York, NY
- L. Xu, U. H. Brinker, in Synthetic Organic Sonochemistry 1998, pp. 344-345 (Ed. J.-L. Luche) (Plenum Press: New York, NY).
- (1998) Synthetic Organic Sonochemistry , pp. 344-345
- Xu, L.¹ Brinker, U.H.²

39
- 0000735216
- doi:10.1021/JA00044A049
- B. M. Trost, C. Pedregal, J. Am. Chem. Soc. 1992, 114, 7292. doi:10.1021/JA00044A049
- (1992) J. Am. Chem. Soc. , vol.114 , pp. 7292
- Trost, B.M.¹ Pedregal, C.²

40
- 0037169069
- Regio- and stereoselective dimerization of terminal alkynes to enynes catalyzed by a palladium/imidazolium system
- DOI 10.1021/jo010837s
- C. Yang, S. P. Nolan, J. Org. Chem. 2002, 67, 591. doi:10.1021/JO010837S (Pubitemid 34101267)
- (2002) Journal of Organic Chemistry , vol.67 , Issue.2 , pp. 591-593
- Yang, C.¹ Nolan, S.P.²

41
- 0002714675
- doi:10.1021/JO00408A041
- W. C. Still, M. Kahn, A. Mitra, J. Org. Chem. 1978, 43, 2923. doi:10.1021/JO00408A041
- (1978) J. Org. Chem. , vol.43 , pp. 2923
- Still, W.C.¹ Kahn, M.² Mitra, A.³

42
- 5244370033
- doi:10.1021/OM9503712
- A. B. Pangborn, M. A. Giardello, R. H. Grubbs, R. K. Rosen, F. J. Timmers, Organometallics 1996, 15, 1518. doi:10.1021/OM9503712
- (1996) Organometallics , vol.15 , pp. 1518
- Pangborn, A.B.¹ Giardello, M.A.² Grubbs, R.H.³ Rosen, R.K.⁴ Timmers, F.J.⁵

43
- 0031059866
- Processing of X-ray diffraction data collected in oscillation mode
- DENZO-SMN:, Eds C. W. Carter Jr, R. M. Sweet Academic Press: New York, NY
- DENZO-SMN: Z. Otwinowski, W. Minor, Processing of X-ray diffraction data collected in oscillation mode, in Methods in Enzymology, Volume 276: Macromolecular Crystallography, Part A 1997, pp. 307-326 (Eds C. W. Carter Jr, R. M. Sweet) (Academic Press: New York, NY).
- (1997) Methods in Enzymology, Volume 276: Macromolecular Crystallography, Part A , pp. 307-326
- Otwinowski, Z.¹ Minor, W.²

44
- 0000604488
- SIR92
- SIR92: A. Altomare, G. Cascarano, C. Giacovazzo, A. Guagliardi, M. C. Burla, G. Polidori, M. Camalli, J. Appl. Cryst. 1994, 27, 435.
- (1994) J. Appl. Cryst. , vol.27 , pp. 435
- Altomare, A.¹ Cascarano, G.² Giacovazzo, C.³ Guagliardi, A.⁴ Burla, M.C.⁵ Polidori, G.⁶ Camalli, M.⁷

45
- 1242313195
- doi:10.1107/S0021889803021800
- P. W. Betteridge, J. R. Carruthers, R. I. Cooper, K. Prout, D. J. Watkin, J. Appl. Cryst. 2003, 36, 1487. doi:10.1107/S0021889803021800
- (2003) J. Appl. Cryst. , vol.36 , pp. 1487
- Betteridge, P.W.¹ Carruthers, J.R.² Cooper, R.I.³ Prout, K.⁴ Watkin, D.J.⁵

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