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Chemistry - A European Journal

Volumn 17, Issue 35, 2011, Pages 9731-9737

Synthesis of the anti-HIV agent (-)-hyperolactone C by using oxonium ylide formation-rearrangement

(2) Hodgson, David M a Man, Stanislav a

a UNIVERSITY OF OXFORD (United Kingdom)

Author keywords

hyperolactone; oxonium ylide; rhodium catalysis; sigmatropic rearrangement; total synthesis

Indexed keywords

HYPEROLACTONE; OXONIUM; RHODIUM CATALYSIS; SIGMATROPIC REARRANGEMENTS; TOTAL SYNTHESIS;

ETHERS; RHODIUM; STYRENE;

CATALYSIS;

ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; CATION; EPOXIDE; FURAN DERIVATIVE; HYDRONIUM ION; HYPEROLACTONE C; RHODIUM; STYRENE OXIDE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ANTI-HIV AGENTS; CATALYSIS; EPOXY COMPOUNDS; FURANS; MOLECULAR STRUCTURE; ONIUM COMPOUNDS; RHODIUM; STEREOISOMERISM;

EID: 80051763668 PISSN: 09476539 EISSN: 15213765 Source Type: Journal
DOI: 10.1002/chem.201101082 Document Type: Article

Times cited : (40)

References (44)

1
- 0029110340
- Y. Aramaki, K. Chiba, M. Tada, Phytochemistry 1995, 38, 1419-1421
- (1995) Phytochemistry , vol.38 , pp. 1419-1421
- Aramaki, Y.¹ Chiba, K.² Tada, M.³

2
- 18144379227
- oo 2176
- S. L. Crockett, W. Schühly, F. Belaj, I. A. Khan, Acta Crystallogr. Sect. E 2004, 60, o 2174 -o 2176
- (2004) Acta Crystallogr. Sect. e , vol.60 , pp. 2174
- Crockett, S.L.¹ Schühly, W.² Belaj, F.³ Khan, I.A.⁴

3
- 18144393041
- W. Schühly, S. L. Crockett, W. M. F. Fabian, Chirality 2005, 17, 250-256.
- (2005) Chirality , vol.17 , pp. 250-256
- Schühly, W.¹ Crockett, S.L.² Fabian, W.M.F.³

4
- 22244469111
- N. Tanaka, M. Okasaka, Y. Ishimaru, Y. Takaishi, M. Sato, M. Okamoto, T. Oshikawa, S. U. Ahmed, L. M. Consentino, K.-H. Lee, Org. Lett. 2005, 7, 2997-2999.
- (2005) Org. Lett. , vol.7 , pp. 2997-2999
- Tanaka, N.¹ Okasaka, M.² Ishimaru, Y.³ Takaishi, Y.⁴ Sato, M.⁵ Okamoto, M.⁶ Oshikawa, T.⁷ Ahmed, S.U.⁸ Consentino, L.M.⁹ Lee, K.-H.¹⁰

5
- 41249100821
- K. C. Nicolaou, D. Sarlah, D. M. Shaw, Angew. Chem. 2007, 119, 4792-4795
- (2007) Angew. Chem. , vol.119 , pp. 4792-4795
- Nicolaou, K.C.¹ Sarlah, D.² Shaw, D.M.³

6
- 34347226722
- Angew. Chem. Int. Ed. 2007, 46, 4708-4711
- (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 4708-4711

7
- 50249115561
- K. C. Nicolaou, T. R. Wu, D. Sarlah, D. M. Shaw, E. Rowcliffe, D. R. Burton, J. Am. Chem. Soc. 2008, 130, 11114-11121; see also
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 11114-11121
- Nicolaou, K.C.¹ Wu, T.R.² Sarlah, D.³ Shaw, D.M.⁴ Rowcliffe, E.⁵ Burton, D.R.⁶

8
- 77954339416
- K. C. Nicolaou, S. Sanchini, T. R. Wu, D. Sarlah, Chem. Eur. J. 2010, 16, 7678-7682
- (2010) Chem. Eur. J. , vol.16 , pp. 7678-7682
- Nicolaou, K.C.¹ Sanchini, S.² Wu, T.R.³ Sarlah, D.⁴

9
- 79955551140
- K. C. Nicolaou, S. Sanchini, D. Sarlah, G. Lu, T. R. Wu, D. K. Nomura, B. F. Cravatt, B. Cubit, J. C de La Torre, D. R. Burton, Proc. Natl. Acad. Sci. USA 2011, 108, 6715-6720.
- (2011) Proc. Natl. Acad. Sci. USA , vol.108 , pp. 6715-6720
- Nicolaou, K.C.¹ Sanchini, S.² Sarlah, D.³ Lu, G.⁴ Wu, T.R.⁵ Nomura, D.K.⁶ Cravatt, B.F.⁷ Cubit, B.⁸ De La Torre, J.C.⁹ Burton, D.R.¹⁰

10
- 0035082665
- T. Ueki, M. Doe, R. Tanaka, Y. Morimoto, K. Yoshihara, T, Kinoshita, J. Heterocycl. Chem. 2001, 38, 165-172.
- (2001) J. Heterocycl. Chem. , vol.38 , pp. 165-172
- Ueki, T.¹ Doe, M.² Tanaka, R.³ Morimoto, Y.⁴ Yoshihara, K.⁵ Kinoshita, T.⁶

11
- 3042631720
- G. A. Kraus, J. Wei, J. Nat. Prod. 2004, 67, 1039-1040.
- (2004) J. Nat. Prod. , vol.67 , pp. 1039-1040
- Kraus, G.A.¹ Wei, J.²

12
- 77954323881
- C. Du, L. Li, Y. Li, Z. Xie, Angew. Chem. 2009, 121, 7993-7996
- (2009) Angew. Chem. , vol.121 , pp. 7993-7996
- Du, C.¹ Li, L.² Li, Y.³ Xie, Z.⁴

13
- 70349673170
- Angew. Chem. Int. Ed. 2009, 48, 7853-7856 (corrigendum
- (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 7853-7856

14
- 80051722505
- C. Du, L. Li, Y. Li, Z. Xie, Angew. Chem. 2009, 121, 9375
- (2009) Angew. Chem. , vol.121 , pp. 9375
- Du, C.¹ Li, L.² Li, Y.³ Xie, Z.⁴

15
- 73049098310
- Angew. Chem. Int. Ed. 2009, 48, 9211)
- (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 9211

16
- 79956126801
- Y. Wu, C. Du, C. Hu, Y. Li, Z. Xie, J. Org. Chem. 2011, 76, 4075-4081.
- (2011) J. Org. Chem. , vol.76 , pp. 4075-4081
- Wu, Y.¹ Du, C.² Hu, C.³ Li, Y.⁴ Xie, Z.⁵

17
- 60949107620
- D. M. Hodgson, D. Angrish, S. P. Erickson, J. Kloesges, C. H. Lee, Org. Lett. 2008, 10, 5553-5556.
- (2008) Org. Lett. , vol.10 , pp. 5553-5556
- Hodgson, D.M.¹ Angrish, D.² Erickson, S.P.³ Kloesges, J.⁴ Lee, C.H.⁵

18
- 33645895004
- K. Kundu, M. P. Doyle, Tetrahedron: Asymmetry 2006, 17, 574-577.
- (2006) Tetrahedron: Asymmetry , vol.17 , pp. 574-577
- Kundu, K.¹ Doyle, M.P.²

19
- 80051738909
- See the Supporting Information for details.
- See the Supporting Information for details.

20
- 0033597733
- S. Kiyooka, M. A. Hena, J. Org. Chem. 1999, 64, 5511-5523
- (1999) J. Org. Chem. , vol.64 , pp. 5511-5523
- Kiyooka, S.¹ Hena, M.A.²

21
- 0037145006
- R. Villano, M. De Rosa, C. Salerno, A. Soriente, A. Scettri, Tetrahedron: Asymmetry 2002, 13, 1949-1952
- (2002) Tetrahedron: Asymmetry , vol.13 , pp. 1949-1952
- Villano, R.¹ De Rosa, M.² Salerno, C.³ Soriente, A.⁴ Scettri, A.⁵

22
- 0028272209
- M. Hayashi, T. Inoue, Y. Miyamoto, N. Oguni, Tetrahedron 1994, 50, 4385-4398
- (1994) Tetrahedron , vol.50 , pp. 4385-4398
- Hayashi, M.¹ Inoue, T.² Miyamoto, Y.³ Oguni, N.⁴

23
- 0039894012
- M. Hayashi, K. Yoshimoto, N. Hirata, K. Tanaka, N. Oguni, K. Harada, A. Matsushita, Y. Kawachi, H. Sasaki, Isr. J. Chem. 2001, 41, 241-246
- (2001) Isr. J. Chem. , vol.41 , pp. 241-246
- Hayashi, M.¹ Yoshimoto, K.² Hirata, N.³ Tanaka, K.⁴ Oguni, N.⁵ Harada, K.⁶ Matsushita, A.⁷ Kawachi, Y.⁸ Sasaki, H.⁹

24
- 0032433212
- K. Narkunan, B.-J. Uang, Synthesis 1998, 1713-1714.
- (1998) Synthesis , pp. 1713-1714
- Narkunan, K.¹ Uang, B.-J.²

25
- 67651089980
- In this paper, both allylation, using allyl trichloroacetimidate, and diazo transfer have been reported on the corresponding Me ester of 18; yields of ∼50% and >90%, respectively were indicated in correspondence from Professor Yakura.
- T. Yakura, K. Matsui, K. Matsuzaka, M. Yamashita, Heterocycles 2009, 79, 353-358. In this paper, both allylation, using allyl trichloroacetimidate, and diazo transfer have been reported on the corresponding Me ester of 18; yields of ∼50% and >90%, respectively were indicated in correspondence from Professor Yakura.
- (2009) Heterocycles , vol.79 , pp. 353-358
- Yakura, T.¹ Matsui, K.² Matsuzaka, K.³ Yamashita, M.⁴

26
- 13444309335
- C. Xu, C. Yuan, Tetrahedron 2005, 61, 2169-2186.
- (2005) Tetrahedron , vol.61 , pp. 2169-2186
- Xu, C.¹ Yuan, C.²

27
- 0035833084
- A. Cosp, P. Romea, F. Urpí, J. Vilarrasa, Tetrahedron Lett. 2001, 42, 4629-4631
- (2001) Tetrahedron Lett. , vol.42 , pp. 4629-4631
- Cosp, A.¹ Romea, P.² Urpí, F.³ Vilarrasa, J.⁴

28
- 0038391500
- A. Cosp, I. Larrosa, I. Vilasís, P. Romea, F. Urpí, J. Vilarrasa, Synlett 2003, 1109-1112
- (2003) Synlett , pp. 1109-1112
- Cosp, A.¹ Larrosa, I.² Vilasís, I.³ Romea, P.⁴ Urpí, F.⁵ Vilarrasa, J.⁶

29
- 43149102475
- J. Baiget, A. Cosp, E. Gálvez, L. Gómez-Pinal, P. Romea, F. Urpí, Tetrahedron 2008, 64, 5637-5644
- (2008) Tetrahedron , vol.64 , pp. 5637-5644
- Baiget, J.¹ Cosp, A.² Gálvez, E.³ Gómez-Pinal, L.⁴ Romea, P.⁵ Urpí, F.⁶

30
- 66149126128
- E. Gálvez, P. Romea, F. Urpí, Org. Synth. 2009, 86, 81-91.
- (2009) Org. Synth. , vol.86 , pp. 81-91
- Gálvez, E.¹ Romea, P.² Urpí, F.³

31
- 0028831530
- J. B. Brogan, J. E. Richard, C. K. Zercher, Synth. Commun. 1995, 25, 587-593.
- (1995) Synth. Commun. , vol.25 , pp. 587-593
- Brogan, J.B.¹ Richard, J.E.² Zercher, C.K.³

32
- 0002930478
- D. W. Brooks, L. D.-L. Lu, S. Masamune, Angew. Chem. 1979, 91, 76-77
- (1979) Angew. Chem. , vol.91 , pp. 76-77
- Brooks, D.W.¹ Lu, L.D.-L.² Masamune, S.³

33
- 4544303707
- Angew. Chem. Int. Ed. Engl. 1979, 18, 72-74.
- (1979) Angew. Chem. Int. Ed. Engl. , vol.18 , pp. 72-74

34
- 0037138704
- Styrene oxide is readily (commercially) available in high e.r. by Jacobsen hydrolytic kinetic resolution.
- Styrene oxide is readily (commercially) available in high e.r. by Jacobsen hydrolytic kinetic resolution:, S. E. Schaus, B. D. Brandes, J. F. Larrow, M. Tokunaga, K. B. Hansen, A. E. Gould, M. E. Furrow, E. N. Jacobsen, J. Am. Chem. Soc. 2002, 124, 1307-1315.
- (2002) J. Am. Chem. Soc. , vol.124 , pp. 1307-1315
- Schaus, S.E.¹ Brandes, B.D.² Larrow, J.F.³ Tokunaga, M.⁴ Hansen, K.B.⁵ Gould, A.E.⁶ Furrow, M.E.⁷ Jacobsen, E.N.⁸

35
- 0026720195
- D. Mitchell, T. M. Koenig, Tetrahedron Lett. 1992, 33, 3281-3284
- (1992) Tetrahedron Lett. , vol.33 , pp. 3281-3284
- Mitchell, D.¹ Koenig, T.M.²

36
- 0028901322
- D. Mitchell, T. M. Koenig, Synth. Commun. 1995, 25, 1231-1238.
- (1995) Synth. Commun. , vol.25 , pp. 1231-1238
- Mitchell, D.¹ Koenig, T.M.²

37
- 0037145055
- A. Kamal, G. B. R. Khanna, R. Ramu, Tetrahedron: Asymmetry 2002, 13, 2039-2051.
- (2002) Tetrahedron: Asymmetry , vol.13 , pp. 2039-2051
- Kamal, A.¹ Khanna, G.B.R.² Ramu, R.³

38
- 39149089631
- D.-Y. Ma, D.-X. Wang, J. Pan, Z.-T. Huang, M.-X. Wang, Tetrahedron: Asymmetry 2008, 19, 322-329.
- (2008) Tetrahedron: Asymmetry , vol.19 , pp. 322-329
- Ma, D.-Y.¹ Wang, D.-X.² Pan, J.³ Huang, Z.-T.⁴ Wang, M.-X.⁵

39
- 8744253296
- H. Shin, B. S. Choi, K. K. Lee, H.-W. Choi, J. H. Chang, K. W. Lee, D. H. Nam, N.-S. Kim, Synthesis 2004, 2629-2632.
- (2004) Synthesis , pp. 2629-2632
- Shin, H.¹ Choi, B.S.² Lee, K.K.³ Choi, H.-W.⁴ Chang, J.H.⁵ Lee, K.W.⁶ Nam, D.H.⁷ Kim, N.-S.⁸

40
- 0004026247
- Oxford University Press, Oxford
- Nitrogen, Oxygen and Sulfur Ylide Chemistry (Ed.:, J. S. Clark,), Oxford University Press, Oxford, 2002, pp. 1-113.
- (2002) Nitrogen, Oxygen and Sulfur Ylide Chemistry , pp. 1-113
- Clark, J.S.¹

41
- 0343444914
- I. Ryu, S. Murai, Y. Hatayama, N. Sonoda, Tetrahedron Lett. 1978, 19, 3455-3458
- (1978) Tetrahedron Lett. , vol.19 , pp. 3455-3458
- Ryu, I.¹ Murai, S.² Hatayama, Y.³ Sonoda, N.⁴

42
- 14644388127
- C.-L. Chin, D. D.-P. Tran, K.-S. Shia, H.-J. Liu, Synlett 2005, 417-420.
- (2005) Synlett , pp. 417-420
- Chin, C.-L.¹ Tran, D.D.-P.² Shia, K.-S.³ Liu, H.-J.⁴

43
- 77955310072
- R. F. B. Cox, R. T. Stormont, Org. Synth. 1935, 15, 1-2.
- (1935) Org. Synth. , vol.15 , pp. 1-2
- Cox, R.F.B.¹ Stormont, R.T.²

44
- 0842285257
- P. N. Liu, P. M. Gu, F. Wang, Y. Q. Tu, Org. Lett. 2004, 6, 169-172.
- (2004) Org. Lett. , vol.6 , pp. 169-172
- Liu, P.N.¹ Gu, P.M.² Wang, F.³ Tu, Y.Q.⁴

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