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Volumn 12, Issue 4, 2014, Pages 667-672

The first synthesis of (-)-isoambreinolide, (+)-vitexifolin D and (+)-vitedoin B

(11) Bouanou, Hanane a Tapia, Rubén a Cano, M José a Ramos, Jose M a Alvarez, Esteban a Boulifa, Ettahir b Dahdouh, Abdelaziz b Mansour, Ahmed I b Alvarez Manzaneda, Ramón c Chahboun, Rachid a Alvarez Manzaneda, Enrique a

a UNIVERSITY OF GRANADA (Spain)

b ABDELMALEK ESSAADI UNIVERSITY (Morocco)

c UNIVERSITY OF ALMERÍA (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

POSITIVE IONS;

HIGH YIELD; TRIPHENYL PHOSPHINES; UNSATURATED CARBOXYLIC ACIDS;

CHEMISTRY;

DITERPENE; LACTONE; SPIRO COMPOUND; VITEDOIN B;

ARTICLE; CHEMISTRY; CONFORMATION; STEREOISOMERISM; SYNTHESIS;

DITERPENES; LACTONES; MOLECULAR CONFORMATION; SPIRO COMPOUNDS; STEREOISOMERISM;

EID: 84890812699 PISSN: 14770520 EISSN: None Source Type: Journal
DOI: 10.1039/c3ob42122h Document Type: Article

Times cited : (9)

References (38)

1
- 84883819726
- T. Asai T. Taniguchi T. Yamamoto K. Monde Y. Oshima Org. Lett. 2013 15 4320 4323
- (2013) Org. Lett. , vol.15 , pp. 4320-4323
- Asai, T.¹ Taniguchi, T.² Yamamoto, T.³ Monde, K.⁴ Oshima, Y.⁵

2
- 84863115766
- M. Liu S. Lin M. Gan M. Chen L. Li S. Wang J. Zi X. Fan Y. Liu Y. Si Y. Yang X. Chen J. Shi Org. Lett. 2012 14 1004 1007
- (2012) Org. Lett. , vol.14 , pp. 1004-1007
- Liu, M.¹ Lin, S.² Gan, M.³ Chen, M.⁴ Li, L.⁵ Wang, S.⁶ Zi, J.⁷ Fan, X.⁸ Liu, Y.⁹ Si, Y.¹⁰ Yang, Y.¹¹ Chen, X.¹² Shi, J.¹³

3
- 79953065098
- A. Bartoli F. Rodier L. Commeiras J.-L. Parrain G. Chouraqui Nat. Prod. Rep. 2011 28 763 782
- (2011) Nat. Prod. Rep. , vol.28 , pp. 763-782
- Bartoli, A.¹ Rodier, F.² Commeiras, L.³ Parrain, J.-L.⁴ Chouraqui, G.⁵

4
- 0036236070
- M. Ono T. Yanaka M. Yamamoto Y. Ito T. Nohara J. Nat. Prod. 2002 65 537 541
- (2002) J. Nat. Prod. , vol.65 , pp. 537-541
- Ono, M.¹ Yanaka, T.² Yamamoto, M.³ Ito, Y.⁴ Nohara, T.⁵

5
- 11844304331
- M. Ono Y. Nishida C. Masuoka J.-C. Li M. Okawa T. Ikeda T. Nohara J. Nat. Prod. 2004 67 2073 2075
- (2004) J. Nat. Prod. , vol.67 , pp. 2073-2075
- Ono, M.¹ Nishida, Y.² Masuoka, C.³ Li, J.-C.⁴ Okawa, M.⁵ Ikeda, T.⁶ Nohara, T.⁷

6
- 0000565676
- Y. Tamura T. Yakura J. I. Haruta Y. Kita J. Org. Chem. 1987 52 3927 3931
- (1987) J. Org. Chem. , vol.52 , pp. 3927-3931
- Tamura, Y.¹ Yakura, T.² Haruta, J.I.³ Kita, Y.⁴

7
- 20544478411
- N. Kotoku H. Tsujita A. Hiramtsu C. Mori N. Koizumi M. Kobayashi Tetrahedron 2005 61 7211 7218
- (2005) Tetrahedron , vol.61 , pp. 7211-7218
- Kotoku, N.¹ Tsujita, H.² Hiramtsu, A.³ Mori, C.⁴ Koizumi, N.⁵ Kobayashi, M.⁶

8
- 0024835729
- D. P. Curran M.-H. Chen E. Spletzeir C. M. Seong C. T. Chang J. Am. Chem. Soc. 1989 111 8872 8878
- (1989) J. Am. Chem. Soc. , vol.111 , pp. 8872-8878
- Curran, D.P.¹ Chen, M.-H.² Spletzeir, E.³ Seong, C.M.⁴ Chang, C.T.⁵

9
- 0035855297
- W. Zhang G. Pugh Tetrahedron Lett. 2001 42 5617 5620
- (2001) Tetrahedron Lett. , vol.42 , pp. 5617-5620
- Zhang, W.¹ Pugh, G.²

10
- 37049077893
- S. Fukuzawa T. Nakanishi T. Fujinami S. Sakai J. Chem. Soc., Chem. Commun. 1986 624 625
- (1986) J. Chem. Soc., Chem. Commun. , pp. 624-625
- Fukuzawa, S.¹ Nakanishi, T.² Fujinami, T.³ Sakai, S.⁴

11
- 0035815122
- C. A. Merlic J. C. Walsh J. Org. Chem. 2001 66 2265 2274
- (2001) J. Org. Chem. , vol.66 , pp. 2265-2274
- Merlic, C.A.¹ Walsh, J.C.²

12
- 37049077699
- R. A. Abramovitch J. A. Hawi J. A. Rodrigues T. R. Trombetta J. Chem. Soc., Chem. Commun. 1986 283 284
- (1986) J. Chem. Soc., Chem. Commun. , pp. 283-284
- Abramovitch, R.A.¹ Hawi, J.A.² Rodrigues, J.A.³ Trombetta, T.R.⁴

13
- 33751343665
- M.-C. Yeh Y.-C. Lee T.-C. Young Synthesis 2006 3621 3624
- (2006) Synthesis , pp. 3621-3624
- Yeh, M.-C.¹ Lee, Y.-C.² Young, T.-C.³

14
- 56449119902
- B.-X. Tang Q. Yin R.-Y. Tang J.-H. Li J. Org. Chem. 2008 73 9008 9011
- (2008) J. Org. Chem. , vol.73 , pp. 9008-9011
- Tang, B.-X.¹ Yin, Q.² Tang, R.-Y.³ Li, J.-H.⁴

15
- 33748622297
- N. Maulide I. E. Markó Org. Lett. 2006 8 3705 3707
- (2006) Org. Lett. , vol.8 , pp. 3705-3707
- Maulide, N.¹ Markó, I.E.²

16
- 46849091997
- M. Nomiya T. Murakami N. Takada T. Okuno Y. Harada M. Hashimoto J. Org. Chem. 2008 73 5039 5047
- (2008) J. Org. Chem. , vol.73 , pp. 5039-5047
- Nomiya, M.¹ Murakami, T.² Takada, N.³ Okuno, T.⁴ Harada, Y.⁵ Hashimoto, M.⁶

17
- 0005714439
- R. D. Miller W. Theis G. Heilig S. Kirchmeyer J. Org. Chem. 1991 56 1453 1463
- (1991) J. Org. Chem. , vol.56 , pp. 1453-1463
- Miller, R.D.¹ Theis, W.² Heilig, G.³ Kirchmeyer, S.⁴

18
- 33644965767
- B. Doroh G. A. Sulikowski Org. Lett. 2006 8 903 906
- (2006) Org. Lett. , vol.8 , pp. 903-906
- Doroh, B.¹ Sulikowski, G.A.²

19
- 27144521210
- C. W. Zapf B. A. Harrison C. Drahl E. J. Sorensen Angew. Chem., Int. Ed. 2005 44 6533 6537
- (2005) Angew. Chem., Int. Ed. , vol.44 , pp. 6533-6537
- Zapf, C.W.¹ Harrison, B.A.² Drahl, C.³ Sorensen, E.J.⁴

20
- 33746217394
- K. C. Nicolaou S. T. Harrison Angew. Chem., Int. Ed. 2006 45 3256 3260
- (2006) Angew. Chem., Int. Ed. , vol.45 , pp. 3256-3260
- Nicolaou, K.C.¹ Harrison, S.T.²

21
- 33746287178
- K. C. Nicolaou R. M. Denton A. Lenzen D. J. Edmonds A. Li R. R. Milburn S. T. Harrison Angew. Chem., Int. Ed. 2006 45 2076 2081
- (2006) Angew. Chem., Int. Ed. , vol.45 , pp. 2076-2081
- Nicolaou, K.C.¹ Denton, R.M.² Lenzen, A.³ Edmonds, D.J.⁴ Li, A.⁵ Milburn, R.R.⁶ Harrison, S.T.⁷

22
- 78649503455
- R. Blanc V. Heran R. Rahmani L. Commeiras J.-L. Pawain Org. Biomol. Chem. 2010 8 5490 5494
- (2010) Org. Biomol. Chem. , vol.8 , pp. 5490-5494
- Blanc, R.¹ Heran, V.² Rahmani, R.³ Commeiras, L.⁴ Pawain, J.-L.⁵

23
- 0008790449
- C. H. Heathcock T. W. Vougeldern Heterocycles 1987 25 75 78
- (1987) Heterocycles , vol.25 , pp. 75-78
- Heathcock, C.H.¹ Vougeldern, T.W.²

24
- 0035859348
- L. Barriault D. H. Deon Org. Lett. 2001 3 1925 1927
- (2001) Org. Lett. , vol.3 , pp. 1925-1927
- Barriault, L.¹ Deon, D.H.²

25
- 48049090242
- T. Taniguchi H. Ishibashi Tetrahedron 2008 64 8773 8779
- (2008) Tetrahedron , vol.64 , pp. 8773-8779
- Taniguchi, T.¹ Ishibashi, H.²

26
- 38749107646
- T. Taniguchi G. Tanabe O. Muraoka H. Ishibashi Org. Lett. 2008 10 197 199
- (2008) Org. Lett. , vol.10 , pp. 197-199
- Taniguchi, T.¹ Tanabe, G.² Muraoka, O.³ Ishibashi, H.⁴

27
- 45249097976
- P. Liu S. Hong S. M. Weinreb J. Am. Chem. Soc. 2008 130 7562 7564
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 7562-7564
- Liu, P.¹ Hong, S.² Weinreb, S.M.³

28
- 84884577494
- M. J. Cano H. Bouanou R. Tapia E. Alvarez R. Alvarez-Manzaneda R. Chahboun E. Alvarez-Manzaneda J. Org. Chem. 2013 78 9196 9204
- (2013) J. Org. Chem. , vol.78 , pp. 9196-9204
- Cano, M.J.¹ Bouanou, H.² Tapia, R.³ Alvarez, E.⁴ Alvarez-Manzaneda, R.⁵ Chahboun, R.⁶ Alvarez-Manzaneda, E.⁷

29
- 84885417354
- R. Tapia M. J. Cano H. Bouanou E. Alvarez R. Alvarez-Manzaneda R. Chahboun E. Alvarez-Manzaneda Chem. Commun. 2013 49 10257 10259
- (2013) Chem. Commun. , vol.49 , pp. 10257-10259
- Tapia, R.¹ Cano, M.J.² Bouanou, H.³ Alvarez, E.⁴ Alvarez-Manzaneda, R.⁵ Chahboun, R.⁶ Alvarez-Manzaneda, E.⁷

30
- 0001245554
- R. Buchecker R. Egli H. Regel-Wild C. Tscharner C. H. Eugster G. Uhde G. Ohloff Helv. Chim. Acta 1973 56 2548 2563
- (1973) Helv. Chim. Acta , vol.56 , pp. 2548-2563
- Buchecker, R.¹ Egli, R.² Regel-Wild, H.³ Tscharner, C.⁴ Eugster, C.H.⁵ Uhde, G.⁶ Ohloff, G.⁷

31
- 4243569733
- V. Jäger W. Kuhn J. Buddrus Tetrahedron Lett. 1986 27 2587 2590
- (1986) Tetrahedron Lett. , vol.27 , pp. 2587-2590
- Jäger, V.¹ Kuhn, W.² Buddrus, J.³

32
- 0035913746
- R. J. Peters M. M. Ravn R. M. Coates R. B. Croteau J. Am. Chem. Soc. 2001 123 8974 8978
- (2001) J. Am. Chem. Soc. , vol.123 , pp. 8974-8978
- Peters, R.J.¹ Ravn, M.M.² Coates, R.M.³ Croteau, R.B.⁴

33
- 0030199646
- Compounds 7 and 8 were synthesized from abietic acid.
- C. Morin N. Nedjar Tetrahedron Lett. 1996 37 4705 4706
- (1996) Tetrahedron Lett. , vol.37 , pp. 4705-4706
- Morin, C.¹ Nedjar, N.²

34
- 84890807891
- PhD thesis, University of Granada, Compounds and 10 were synthesized from (-)-menthol.
- R. Tapia, PhD thesis, University of Granada, 2012
- (2012) , vol.9
- Tapia, R.¹

35
- 84890816078
- PhD thesis, University of Granada, For a brief description of the corresponding carboxylic acid, see
- H. Bouanou, PhD thesis, University of Granada, 2013
- (2013)
- Bouanou, H.¹

36
- 33751343788
- The corresponding carboxylic acid has been recently isolated. See
- D. Burn W. Rigby J. Chem. Soc. 1957 2964 2974
- (1957) J. Chem. Soc. , pp. 2964-2974
- Burn, D.¹ Rigby, W.²

37
- 39149139595
- During their studies on the stereochemistry of marrubiin, McCrindle et al. reported the conversion of ambreinolide into isoambreinolide by treatment with sulphuric acid. These authors indicate a low yield, which is not specified, for this transformation and did not provide evidence for the configurations on the C-8 and C-9 of the final compound. See
- G. Cioffi A. Bader A. Malafronte F. Dal Piaz N. De Tommasi Phytochemistry 2008 69 1005 1012
- (2008) Phytochemistry , vol.69 , pp. 1005-1012
- Cioffi, G.¹ Bader, A.² Malafronte, A.³ Dal Piaz, F.⁴ De Tommasi, N.⁵

38
- 37049139283
- R. A. Appleton J. W. B. Fulke M. S. Henderson R. McCrindle J. Chem. Soc. C 1967 1943 1947
- (1967) J. Chem. Soc. C , pp. 1943-1947
- Appleton, R.A.¹ Fulke, J.W.B.² Henderson, M.S.³ McCrindle, R.⁴

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