SCOPUS 정보 검색 플랫폼

Australian Journal of Chemistry

Volumn 62, Issue 9, 2009, Pages 980-982

Total synthesis of (±)-Vibsanin e

(4) Schwartz, Brett D a Denton, Justin R b Davies, Huw M L c Williams, Craig M a

a UNIVERSITY OF QUEENSLAND (Australia)

b UNIVERSITY AT BUFFALO (United States)

c EMORY UNIVERSITY (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DITERPENES; ENOL ESTERS; TOTAL SYNTHESIS; WILLIAMS;

ESTERS; OLEFINS;

FUNCTIONAL GROUPS;

EID: 70349303786 PISSN: 00049425 EISSN: None Source Type: Journal
DOI: 10.1071/CH09267 Document Type: Conference Paper

Times cited : (22)

References (33)

1
- 17444429909
- (a) K. Kawazu, IUPAC Int. Symp. Chem. Nat. Prod. (11th) 1978, 2, 101.
- (1978) IUPAC Int. Symp. Chem. Nat. Prod. (11th) , vol.2 , pp. 101
- Kawazu, K.¹

2
- 84943953002
- (b) K. Kawazu, Agric. Biol. Chem. 1980, 44, 1367.
- (1980) Agric. Biol. Chem. , vol.44 , pp. 1367
- Kawazu, K.¹

3
- 37049102619
- doi:10.1039/P29800001701
- (c) K. Fukuyama,Y. Katsube, K. Kawazu, J. Chem. Soc., Perkin Trans. II 1980, 1701. doi:10.1039/P29800001701
- (1980) J. Chem. Soc., Perkin Trans. II , pp. 1701
- Fukuyama, K.¹ Katsube, Y.² Kawazu, K.³

4
- 56149086671
- doi:10.1002/CBDV.200890175
- L.-Q. Wang, Y.-G. Chen, J.-J. Xu, Y. Liu, X.-M. Li, Y. Zhao, Chem. Biodivers. 2008, 5, 1879. doi:10.1002/CBDV.200890175
- (2008) Chem. Biodivers. , vol.5 , pp. 1879
- Wang, L.-Q.¹ Chen, Y.-G.² Xu, J.-J.³ Liu, Y.⁴ Li, X.-M.⁵ Zhao, Y.⁶

5
- 17444420593
- Rearranged vibsane-type diterpenes from Viburnum awabuki and photochemical reaction of vibsanin B
- DOI 10.1248/cpb.53.72
- (a) Y. Fukuyama, M. Kubo, H. Minami, H. Yuasa, A. Matsuo, T. Fujii, M. Morisaki, K. Harada, Chem. Pharm. Bull. 2005, 53, 72 and references therein. doi:10.1248/CPB.53.72 (Pubitemid 40879840)
- (2005) Chemical and Pharmaceutical Bulletin , vol.53 , Issue.1 , pp. 72-80
- Fukuyama, Y.¹ Kubo, M.² Minami, H.³ Yuasa, H.⁴ Matsuo, A.⁵ Fujii, T.⁶ Morisaki, M.⁷ Harada, K.⁸

6
- 34548266652
- (b) Y. Fukuyama, T. Esumi, J. Org. Syn. Chem. 2007, 65, 585.
- (2007) J. Org. Syn. Chem. , vol.65 , pp. 585
- Fukuyama, Y.¹ Esumi, T.²

7
- 65549155919
- doi:10.3987/ COM-08-S(F)62
- (c) M. Kubo, Y. Minoshima, D. Arimoto, H. Minami, K. Harada, H. Hioki, Y. Fukuyama, Heterocycles 2009, 77, 539. doi:10.3987/ COM-08-S(F)62
- (2009) Heterocycles , vol.77 , pp. 539
- Kubo, M.¹ Minoshima, Y.² Arimoto, D.³ Minami, H.⁴ Harada, K.⁵ Hioki, H.⁶ Fukuyama, Y.⁷

8
- 0036323385
- New vibsane diterpenes and lupane triterpenes from Viburnum odoratissimum
- DOI 10.1021/np020007p
- (a)Y.-C. Shen, C. V. S. Prakash, L.-T. Wang, C.Y. Chien, M.-C. Hung, J. Nat. Prod. 2002, 65, 1052. doi:10.1021/NP020007P (Pubitemid 34827500)
- (2002) Journal of Natural Products , vol.65 , Issue.7 , pp. 1052-1055
- Shen, Y.-C.¹ Prakash, C.V.S.² Wang, L.-T.³ Chien, C.-T.⁴ Hung, M.-C.⁵

9
- 0942279796
- Vibsane Diterpenoids from the Leaves and Flowers of Viburnum odoratissimum
- DOI 10.1021/np030173c
- (b) Y.-C. Shen, C.-L. Lin, S.-C. Chien, A. T. Khalil, C.-L. Ko, C.-H. Wang, J. Nat. Prod. 2004, 67, 74. doi:10.1021/NP030173C (Pubitemid 38141315)
- (2004) Journal of Natural Products , vol.67 , Issue.1 , pp. 74-77
- Shen, Y.-C.¹ Lin, C.-L.² Chien, S.-C.³ Khalil, A.T.⁴ Ko, C.-L.⁵ Wang, C.-H.⁶

10
- 0344873164
- Vibsanin O, a novel diterpenoid from Viburnum awabuki
- DOI 10.1016/j.tetlet.2003.10.084
- (a) C.-Y. Duh,A.A. H. El-Gamal, S.-K. Wang,Tetrahedron Lett. 2003, 44 , 9321. doi:10.1016/J.TETLET.2003.10.084 (Pubitemid 37485827)
- (2003) Tetrahedron Letters , vol.44 , Issue.52 , pp. 9321-9322
- Duh, C.-Y.¹ El-Gamal, A.A.H.² Wang, S.-K.³

11
- 1642424312
- New Diterpenoids from Viburnum awabuki
- DOI 10.1021/np030447w
- (b)A. A. H. El-Gamal, S. K. Wang, C.-Y. Duh, J. Nat. Prod. 2004, 67, 333. doi:10.1021/NP030447W (Pubitemid 38405691)
- (2004) Journal of Natural Products , vol.67 , Issue.3 , pp. 333-336
- El-Gamal, A.A.H.¹ Wang, S.-K.² Duh, C.-Y.³

12
- 56449120599
- doi:10.1021/JA807133P
- L. Dong, V. A. Gordon, R. L. Grange, J. Johns, P. G. Parsons, A. Porzelle, P. Reddell, H. Schill, C. M. Williams, J. Am. Chem. Soc. 2008, 130, 15262. doi:10.1021/JA807133P
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 15262
- Dong, L.¹ Gordon, V.A.² Grange, R.L.³ Johns, J.⁴ Parsons, P.G.⁵ Porzelle, A.⁶ Reddell, P.⁷ Schill, H.⁸ Williams, C.M.⁹

13
- 54049111472
- doi:10.1021/OL801117E
- A. P.-J. Chen, C. M. Williams, Org. Lett. 2008, 10, 3441. doi:10.1021/ OL801117E
- (2008) Org. Lett. , vol.10 , pp. 3441
- Chen, A.P.-J.¹ Williams, C.M.²

14
- 64049099890
- doi:10.1021/OL802973F
- H. Imagawa, H. Saijo, T. Kurisaki, H. Yamamoto, M. Kubo, Y. Fukuyama, M. Nishizawa, Org. Lett. 2009, 11, 1253. doi:10.1021/ OL802973F
- (2009) Org. Lett. , vol.11 , pp. 1253
- Imagawa, H.¹ Saijo, H.² Kurisaki, T.³ Yamamoto, H.⁴ Kubo, M.⁵ Fukuyama, Y.⁶ Nishizawa, M.⁷

15
- 67650561139
- doi:10.1021/JA9019484
- B. D. Schwartz, J. R. Denton,Y. Lian, H. M. L. Davies, C. M. Williams, J. Am. Chem. Soc. 2009, 131, 8329. doi:10.1021/JA9019484
- (2009) J. Am. Chem. Soc. , vol.131 , pp. 8329
- Schwartz, B.D.¹ Dentony. Lian, J.R.² Davies, H.M.L.³ Williams, C.M.⁴

16
- 0042848832
- Determination of the absolute configuration of vibsanin F by asymmetric synthesis via π-allylpalladium complex
- DOI 10.1016/S0040-4039(03)01537-5
- H.Yuasa, G. Makado,Y. Fukuyama, Tetrahedron Lett. 2003, 44, 6235. doi:10.1016/S0040-4039(03)01537-5 (Pubitemid 36897568)
- (2003) Tetrahedron Letters , vol.44 , Issue.33 , pp. 6235-6239
- Yuasa, H.¹ Makado, G.² Fukuyama, Y.³

17
- 29444442599
- Sequential cycloaddition approach to the tricyclic core of vibsanin E. Total synthesis of (±)-5-epi-10-epi-vibsanin E
- DOI 10.1021/ol052005c
- H. M. L. Davies, Ø. Loe, D. G. Stafford, Org. Lett. 2005, 7, 5561. doi:10.1021/OL052005C (Pubitemid 43010799)
- (2005) Organic Letters , vol.7 , Issue.25 , pp. 5561-5563
- Davies, H.M.L.¹ Loe, O.² Stafford, D.G.³

18
- 34848815404
- Mechanistic studies of UV assisted [4 + 2] cycloadditions in synthetic efforts toward vibsanin E
- DOI 10.1021/ja072090e
- (b) J. Nikolai, Ø. Loe, P. M. Dominiak, O. O. Gerlitz, J. Autschbach, H. M. L. Davies, J. Am. Chem. Soc. 2007, 129, 10763. doi:10.1021/ JA072090E (Pubitemid 350067486)
- (2007) Journal of the American Chemical Society , vol.129 , Issue.35 , pp. 10763-10772
- Nikolai, J.¹ Loe, O.² Dominiak, P.M.³ Gerlitz, O.O.⁴ Autschbach, J.⁵ Davies, H.M.L.⁶

19
- 43549101427
- doi:10.1021/OL702827X
- (a) M. J. Gallen, C. M. Williams, Org. Lett. 2008, 10, 713. doi:10.1021/OL702827X
- (2008) Org. Lett. , vol.10 , pp. 713
- Gallen, M.J.¹ Williams, C.M.²

20
- 33746068471
- In part see doi:10.1002/ ANIE.200504156
- In part see, M. J. Gallen, R. Goumont, T. Clark, F. Terrier, C. M. Williams, Angew. Chem. Int. Ed. 2006, 45, 2929. doi:10.1002/ ANIE.200504156
- (2006) Angew. Chem. Int. Ed. , vol.45 , pp. 2929
- Gallen, M.J.¹ Goumont, R.² Clark, T.³ Terrier, F.⁴ Williams, C.M.⁵

21
- 53849143296
- In part see doi:10.1002/EJOC.200800574
- In full see, M. J. Gallen, C. M. Williams, Eur. J. Org. Chem. 2008, 4697. doi:10.1002/EJOC.200800574
- (2008) Eur. J. Org. Chem. , pp. 4697
- Gallen, M.J.¹ Williams, C.M.²

22
- 28244480787
- Construction of the cyclovibsanin core via a biogenetically modeled approach
- DOI 10.1021/ol051897d
- D. P. Tilly, C. M. Williams, P. V. Bernhardt, Org. Lett. 2005, 7, 5155. doi:10.1021/OL051897D (Pubitemid 41713225)
- (2005) Organic Letters , vol.7 , Issue.23 , pp. 5155-5157
- Tilly, D.P.¹ Williams, C.M.² Bernhardt, P.V.³

23
- 40949088868
- doi:10.1016/J.TETLET. 2008.02.168
- T. Esumi, M. Zhao, T. Kawakami, M. Kukumoto, M. Toyota, Y. Fukuyama, Tetrahedron Lett. 2008, 49, 2692. doi:10.1016/J.TETLET. 2008.02.168
- (2008) Tetrahedron Lett. , vol.49 , pp. 2692
- Esumi, T.¹ Zhao, M.² Kawakami, T.³ Kukumoto, M.⁴ Toyota, M.⁵ Fukuyama, Y.⁶

24
- 50649115490
- doi:10.1016/J.TETASY.2008.08.012
- A. Srikrishna, V. H. Pardeshi, G. Satyanarayana, Tetrahedron Asymmetry 2008, 19, 1984. doi:10.1016/J.TETASY.2008.08.012
- (2008) Tetrahedron Asymmetry , vol.19 , pp. 1984
- Srikrishna, A.¹ Pardeshi, V.H.² Satyanarayana, G.³

25
- 63749086312
- doi:10.1016/J.TETLET.2009.03.040
- G. Mehta, B. A. Bhat, Tetrahedron Lett. 2009, 50, 2474. doi:10.1016/J.TETLET.2009.03.040
- (2009) Tetrahedron Lett. , vol.50 , pp. 2474
- Mehta, G.¹ Bhat, B.A.²

26
- 17444396773
- Expedient construction of the vibsanin E core without the use of protecting groups
- DOI 10.1021/ol0501222
- R. Heim, S. Wiedemann, C. M. Williams, P. V. Bernhardt, Org. Lett. 2005, 7, 1327. doi:10.1021/OL0501222 (Pubitemid 40544111)
- (2005) Organic Letters , vol.7 , Issue.7 , pp. 1327-1329
- Heim, R.¹ Wiedemann, S.² Williams, C.M.³ Bernhardt, P.V.⁴

27
- 33746098889
- doi:10.1002/EJOC.200600246
- B. D. Schwartz, D. P. Tilly, R. Heim, S. Wiedemann, C. M. Williams, P. V. Bernhardt, Eur. J. Org. Chem. 2006, 3181. doi:10.1002/EJOC.200600246
- (2006) Eur. J. Org. Chem. , pp. 3181
- Schwartz, B.D.¹ Tilly, D.P.² Heim, R.³ Wiedemann, S.⁴ Williams, C.M.⁵ Bernhardt, P.V.⁶

28
- 67650536004
- doi:10.3762/BJOC.4.34
- B. D. Schwartz, C. M. Williams, P. V. Bernhardt, Beilstein J. Org. Chem. 2008, 4, 34. doi:10.3762/BJOC.4.34
- (2008) Beilstein J. Org. Chem. , vol.4 , pp. 34
- Schwartz, B.D.¹ Williams, C.M.² Bernhardt, P.V.³

29
- 44349181375
- doi:10.1016/J.TET.2008.04.068
- B. D. Schwartz, C. M. Williams, E. Anders, P. V. Bernhardt, Tetrahedron 2008, 64, 6482. doi:10.1016/J.TET.2008.04.068
- (2008) Tetrahedron , vol.64 , pp. 6482
- Schwartz, B.D.¹ Williams, C.M.² Anders, E.³ Bernhardt, P.V.⁴

30
- 0000074098
- doi:10.1016/0040-4020(89)80077-8
- R. J. Linderman, A. Godfrey, K. Horne, Tetrahedron 1989, 45, 495. doi:10.1016/0040-4020(89)80077-8
- (1989) Tetrahedron , vol.45 , pp. 495
- Linderman, R.J.¹ Godfrey, A.² Horne, K.³

31
- 14544286831
- Total synthesis of sordaricin
- DOI 10.1021/jo048199b
- L. N. Mander, R. J. Thomson, J. Org. Chem. 2005, 70, 1654. doi:10.1021/JO048199B (Pubitemid 40300125)
- (2005) Journal of Organic Chemistry , vol.70 , Issue.5 , pp. 1654-1670
- Mander, L.N.¹ Thomson, R.J.²

32
- 70349374338
- Note: non-stabilized ylids as a general rule give rise to cis (or Z) olefin products, but it has been found[20] that steric hindrance dramatically influences the selectivity in the case of 18, hence the observation of an ~10:1 E/Z ratio observed for synthetic vibsanin E 1
- Note: non-stabilized ylids as a general rule give rise to cis (or Z) olefin products, but it has been found[20] that steric hindrance dramatically influences the selectivity in the case of 18, hence the observation of an ~10:1 E/Z ratio observed for synthetic vibsanin E (1

33
- 70349346513
- See supporting information for comparative 1H and 13C NMR spectra of synthetic and natural vibsanin E 1
- See supporting information for comparative 1H and 13C NMR spectra of synthetic and natural vibsanin E (1

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.