SCOPUS 정보 검색 플랫폼 - 논문 보기

메뉴 건너뛰기

Tetrahedron Letters

Volumn 43, Issue 27, 2002, Pages 4841-4844

Synthesis of (-)-laulimalide: An agent for microtubule stabilization

(4) Williams, David R a Mi, Liang a Mullins, Richard J a Stites, Ryan E a

a INDIANA UNIVERSITY (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENYL GROUP; ALLENE DERIVATIVE; LAULIMALIDE; STABILIZING AGENT; ZINC DERIVATIVE;

ARTICLE; CHELATION; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHIRALITY; CONJUGATE; DRUG SYNTHESIS; ENANTIOSELECTIVITY; MICROTUBULE; STEREOCHEMISTRY;

EID: 0036644261 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/S0040-4039(02)00907-3 Document Type: Article

Times cited : (54)

References (50)

1
- 0001008492
- (1988) J. Org. Chem. , vol.53 , pp. 3644
- Quinoa, E.¹ Kakou, Y.² Crews, R.³

2
- 0023710155
- (1988) J. Org. Chem. , vol.53 , pp. 3644
- Corley, D.G.¹ Herb, R.² Moore, R.E.³ Scheuer, P.J.⁴

3
- 0002792091
- (1996) Chem. Lett. , pp. 255
- Tanaka, J.¹ Higa, T.² Bernardinelli, G.³ Jefford, C.⁴

4
- 0033083045
- (1999) Cancer Res. , vol.59 , pp. 653
- Mooberry, S.L.¹ Tien, G.² Hernandez, A.H.³ Plubrukarn, A.⁴ Davidson, B.S.⁵

5
- 0033551046
- (1999) Proc. Natl. Acad. Sci. USA , vol.96 , pp. 4256
- Ojima, I.¹ Chakravarty, S.² Inoue, T.³ Lin, S.⁴ He, L.⁵ Horwitz, S.B.⁶ Kuduk, S.D.⁷ Danishefsky, S.J.⁸

6
- 0034623543
- (2000) J. Am. Chem. Soc. , vol.122 , pp. 11027
- Ghosh, A.K.¹ Wang, Y.²

7
- 0035807553
- (2001) Org. Lett. , vol.3 , pp. 3149
- Paterson, I.¹ De Savi, C.² Tudge, M.³

8
- 0035980297
- (2001) J. Am. Chem. Soc. , vol.123 , pp. 10764
- Enev, V.S.¹ Kaehlig, H.² Mulzer, J.³

9
- 0035887174
- (2001) Angew. Chem., Int. Ed. , vol.40 , pp. 3842
- Mulzer, J.¹ Öhler, E.²

10
- 0037033212
- (2002) Tetrahedron Lett. , vol.43 , pp. 213
- Sivaramakrishan, A.¹ Nadolskit, G.T.² McAlexander, I.A.³ Davidson, B.S.⁴

11
- 0035966618
- (2001) Tetrahedron Lett. , vol.42 , pp. 801
- Messenger, B.T.¹ Davidson, B.S.²

12
- 0034175522
- (2000) Tetrahedron Lett. , vol.41 , pp. 2319
- Ghosh, A.K.¹ Wang, Y.²

13
- 0035966568
- (2001) Tetrahedron Lett. , vol.42 , pp. 797
- Nadolski, G.T.¹ Davidson, B.S.²

14
- 0034659844
- (2000) Tetrahedron Lett. , vol.41 , pp. 4705
- Ghosh, A.K.¹ Wang, Y.²

15
- 0034641440
- (2000) Tetrahedron Lett. , vol.41 , pp. 6323
- Dorling, E.K.¹ Öhler, E.² Mulzer, J.³

16
- 0033991982
- (2000) Tetrahedron Lett. , vol.41 , pp. 33
- Mulzer, J.¹ Hanbauer, M.²

17
- 0032536002
- (1998) Tetrahedron: Asymmetry , vol.9 , pp. 1
- Ghosh, A.K.¹ Mathivanan, P.² Cappiello, J.³

18
- 0035945742
- (2001) Org. Lett. , vol.3 , pp. 213
- Paterson, I.¹ De Savi, C.² Tudge, M.³

19
- 0001030047
- (1998) Synlett , pp. 1209
- Shimizu, A.¹ Nishiyama, S.²

20
- 0030785757
- (1997) Tetrahedron Lett. , vol.38 , pp. 6011
- Shimizu, A.¹ Nishiyama, S.²

21
- 0035966568
- (2001) Tetrahedron Lett. , vol.42 , pp. 797
- Nadolski, G.T.¹ Davidson, B.S.²

22
- 0032192220
- (1998) Tetrahedron Lett. , vol.39 , pp. 7251
- Williams, D.R.¹ Brooks, D.A.² Meyer, K.G.³ Clark, M.P.⁴

23
- 0035977646
- (2001) J. Am. Chem. Soc. , vol.123 , pp. 765
- Williams, D.R.¹ Meyer, K.G.²

24
- 0034611509
- (2000) Org. Lett. , vol.2 , pp. 945
- Williams, D.R.¹ Myers, B.J.² Mi, L.³

25
- 0033606291
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 4924
- Williams, D.R.¹ Brooks, D.A.² Berliner, M.A.³

26
- 0032483753
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 11198
- Williams, D.R.¹ Kissel, W.S.²

27
- 0032547974
- (1998) Tetrahedron Lett. , vol.39 , pp. 8593
- Williams, D.R.¹ Kissel, W.S.² Li, J.J.³

28
- 0037071136
- (2002) Tetrahedron Lett. , vol.43 , pp. 3723
- Williams, D.R.¹ Kissel, W.S.² Li, J.J.³ Mullins, R.J.⁴

29
- 12044258371
- (1993) Chem. Rev. , vol.93 , pp. 2779
- Ferrier, R.J.¹ Middleton, S.²

30
- 84985531889
- (1986) Angew Chem., Int. Ed. , vol.25 , pp. 947
- Yamamoto, Y.¹

31
- 33847805195
- (1974) J. Am. Chem. Soc. , vol.96 , pp. 7807
- Danishefsky, S.¹ Kitahara, T.²

32
- 0000936493
- (1998) J. Org. Chem. , vol.63 , pp. 403
- Jacobsen, E.N.¹ Schaus, S.E.² Brånalt, J.³

33
- 84995731894
- 9) isomer exhibited a pair of multiplets at δ 1.79 and δ 1.61

34
- 0002313620
- (1996) Chem. Rev. , vol.96 , pp. 31
- Marshall, J.A.¹

35
- 84995718325
- The Grignard reagent was purchased from Aldrich as a 1.0 M solution in ether. Optimal yields were obtained when the reagent was used from a previously unopened bottle

36
- 0001650678
- (1989) Tetrahedron , vol.45 , pp. 5877
- Lee, T.V.¹ Channon, J.A.² Cregg, C.³ Porter, J.R.⁴ Roden, F.S.⁵ Yeoh, H.T.⁶

37
- 0009479520
- (1984) J. Org. Chem. , vol.15 , pp. 2835
- Masamune, S.¹ Ma, P.² Okumoto, H.³ Ellingboe, J.W.⁴ Ito, Y.⁵

38
- 0021149831
- (1984) J. Am. Chem. Soc. , vol.106 , pp. 2949
- Williams, D.R.¹ Sit, S.-Y.²

39
- 0028342831
- (1994) Tetrahedron Lett. , vol.35 , pp. 5197
- Wipf, P.¹ Xu, W.²

40
- 0001219708
- (1998) J. Org. Chem. , vol.63 , pp. 6454
- Wipf, P.¹ Ribe, S.²

41
- 84995717648
- note

42
- 84995729598
- AB than the corresponding anti-diastereomer

43
- 84995727645
- AB=11.2 Hz)

44
- 0001263185
- (1992) J. Am. Chem. Soc. , vol.114 , pp. 5426
- Fu, G.C.¹ Grubbs, R.H.²

45
- 0002464862
- (1979) Aldrichim. Acta , vol.12 , pp. 63
- Sharpless, K.B.¹ Verhoeven, T.R.²

46
- 84995727632
- note

47
- 0001616071
- (1979) Bull. Chem. Soc. Jpn. , vol.53 , pp. 1989
- Inanaga, J.¹ Hirata, K.² Saeki, T.³ Yamaguchi, M.⁴

48
- 84995731626
- We gratefully acknowledge the assistance of Professor Crimmins (University of North Carolina, Chapel Hill) for providing us with details of conditions for deprotection of 19, NMR spectra of the bis-TBS ether 19 for our comparisons, and a preprint of the successful total synthesis of 1 recently developed in his laboratories. Crimmins, M. T.; Stanton, M. G.; Allwein, S. P. J. Am. Chem. Soc. 2002, ASAP

49
- 84995715486
- We thank Professor Phillip Crews at the University of California, Santa Cruz for a sample and NMR spectra of naturally occurring (-)-laulimalide (fijianolide B)

50
- 84995722401
- note

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.