SCOPUS 정보 검색 플랫폼

Volumn 17, Issue 30, 2011, Pages 8487-8494

Total synthesis of (+)-(2′S,3′R)-zoapatanol exploiting the B-alkyl Suzuki reaction and the nucleophilic potential of the sulfinyl group

(2) Raghavan, Sadagopan a Sudheerbabu, Vaddela a

a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY (India)

Author keywords

asymmetric synthesis; cross coupling; natural products; oxepanes; total synthesis

Indexed keywords

ASYMMETRIC SYNTHESIS; CROSS-COUPLINGS; NATURAL PRODUCTS; OXEPANES; TOTAL SYNTHESIS;

FUNCTIONAL GROUPS; OLEFINS; STEREOCHEMISTRY; STEREOSELECTIVITY;

SYNTHESIS (CHEMICAL);

CONTRACEPTIVE AGENT; OXEPINE DERIVATIVE; ZOAPATANOL;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

CONTRACEPTIVE AGENTS; MOLECULAR STRUCTURE; OXEPINS;

EID: 79960323004 PISSN: 09476539 EISSN: 15213765 Source Type: Journal
DOI: 10.1002/chem.201003666 Document Type: Article

Times cited : (16)

References (43)

1
- 0000754153
- S. D. Levine, R. D. Adams, R. Chen, M. L. Cotter, A. F. Hirsch, V. V. Kane, R. M. Kanojia, C. J. Shaw, M. P. Wachter, E. Chin, R. Huetteman, P. Ostrowski, J. L. Mateos, L. Noriega, A. Guzman, A. Mijarez, L. Tovar, J. Am. Chem. Soc. 1979, 101, 3404.
- (1979) J. Am. Chem. Soc. , vol.101 , pp. 3404
- Levine, S.D.¹ Adams, R.D.² Chen, R.³ Cotter, M.L.⁴ Hirsch, A.F.⁵ Kane, V.V.⁶ Kanojia, R.M.⁷ Shaw, C.J.⁸ Wachter, M.P.⁹ Chin, E.¹⁰ Huetteman, R.¹¹ Ostrowski, P.¹² Mateos, J.L.¹³ Noriega, L.¹⁴ Guzman, A.¹⁵ Mijarez, A.¹⁶ Tovar, L.¹⁷

2
- 0012161517
- Y. Oshima, G. A. Cordial, H. S. Fong, Phytochemistry 1986, 25, 2567
- (1986) Phytochemistry , vol.25 , pp. 2567
- Oshima, Y.¹ Cordial, G.A.² Fong, H.S.³

3
- 0343770601
- L. Quijano, J. S. Calderon, N. K. Fisher, Phytochemistry 1985, 24, 2337.
- (1985) Phytochemistry , vol.24 , pp. 2337
- Quijano, L.¹ Calderon, J.S.² Fisher, N.K.³

4
- 0021837410
- R. M. Kanojia, E. Chin, C. Smith, R. Chen, D. Rowand, S. D. Levine, M. P. Wachter, R. E. Adams, D. W. Hahn, J. Med. Chem. 1985, 28, 796
- (1985) J. Med. Chem. , vol.28 , pp. 796
- Kanojia, R.M.¹ Chin, E.² Smith, C.³ Chen, R.⁴ Rowand, D.⁵ Levine, S.D.⁶ Wachter, M.P.⁷ Adams, R.E.⁸ Hahn, D.W.⁹

5
- 0019474265
- D. W. Hahn, E. W. Ericson, V. Lai, A. Probst, Contraception 1981, 23, 133
- (1981) Contraception , vol.23 , pp. 133
- Hahn, D.W.¹ Ericson, E.W.² Lai, V.³ Probst, A.⁴

6
- 0006398952
- D. W. Hahn, A. J. Tobia, H. E. Rosenthale, J. L. McGuire, Contraception 1984, 26, 133.
- (1984) Contraception , vol.26 , pp. 133
- Hahn, D.W.¹ Tobia, A.J.² Rosenthale, H.E.³ McGuire, J.L.⁴

7
- 0019128313
- R. Chen, D. A. Rowand, J. Am. Chem. Soc. 1980, 102, 6609
- (1980) J. Am. Chem. Soc. , vol.102 , pp. 6609
- Chen, R.¹ Rowand, D.A.²

8
- 0001293261
- K. C. Nicolaou, D. E. Claremon, W. E. Barnett, J. Am. Chem. Soc. 1980, 102, 6611
- (1980) J. Am. Chem. Soc. , vol.102 , pp. 6611
- Nicolaou, K.C.¹ Claremon, D.E.² Barnett, W.E.³

9
- 0019402263
- V. V. Kane, D. L. Doyle, Tetrahedron Lett. 1981, 22, 3027
- (1981) Tetrahedron Lett. , vol.22 , pp. 3027
- Kane, V.V.¹ Doyle, D.L.²

10
- 37049107936
- R. C. Cookson, N. J. Liverton, J. Chem. Soc. Perkin Trans. 1 1985, 1589
- (1985) J. Chem. Soc. Perkin Trans. 1 , pp. 1589
- Cookson, R.C.¹ Liverton, N.J.²

11
- 0024340606
- P. J. Kocienski, C. J. Love, R. J. Whitby, Tetrahedron 1989, 45, 3839; for synthetic approaches, see
- (1989) Tetrahedron , vol.45 , pp. 3839
- Kocienski, P.J.¹ Love, C.J.² Whitby, R.J.³

12
- 37049068726
- M. J. Davies, J. C. Heslin, C. J. Moody, J. Chem. Soc. Perkin Trans. 1 1989, 2473
- (1989) J. Chem. Soc. Perkin Trans. 1 , pp. 2473
- Davies, M.J.¹ Heslin, J.C.² Moody, C.J.³

13
- 0028232476
- G. Pain, D. Desmaele, J. d'Angelo, Tetrahedron Lett. 1994, 35, 3085
- (1994) Tetrahedron Lett. , vol.35 , pp. 3085
- Pain, G.¹ Desmaele, D.² D'Angelo, J.³

14
- 0029953154
- T. K. M. Shing, C.-H. Wong, T. Yip, Tetrahedron: Asymmetry 1996, 7, 1323
- (1996) Tetrahedron: Asymmetry , vol.7 , pp. 1323
- Shing, T.K.M.¹ Wong, C.-H.² Yip, T.³

15
- 0035855353
- H. Ovaa, G. A. vanderMarel, J. H. vanBoom, Tetrahedron Lett. 2001, 42, 5749
- (2001) Tetrahedron Lett. , vol.42 , pp. 5749
- Ovaa, H.¹ Vandermarel, G.A.² Vanboom, J.H.³

16
- 38349092278
- I. García, M. Perez, P. Besada, G. Gomez, Y. Fall, Tetrahedron Lett. 2008, 49, 1344.
- (2008) Tetrahedron Lett. , vol.49 , pp. 1344
- García, I.¹ Perez, M.² Besada, P.³ Gomez, G.⁴ Fall, Y.⁵

17
- 0037714557
- B. M. Trost, P. D. Greenspan, H. Geissler, J. H. Kim, N. Greeves, Angew. Chem. 1994, 106, 2296
- (1994) Angew. Chem. , vol.106 , pp. 2296
- Trost, B.M.¹ Greenspan, P.D.² Geissler, H.³ Kim, J.H.⁴ Greeves, N.⁵

18
- 33749019404
- Angew. Chem. Int. Ed. Engl. 1994, 33, 2182
- (1994) Angew. Chem. Int. Ed. Engl. , vol.33 , pp. 2182

19
- 3142683072
- C. Taillier, V. Bellosta, J. Cossy, Org. Lett. 2004, 6, 2149
- (2004) Org. Lett. , vol.6 , pp. 2149
- Taillier, C.¹ Bellosta, V.² Cossy, J.³

20
- 15444379755
- C. Taillier, B. Gille, V. Bellosta, J. Cossy, J. Org. Chem. 2005, 70, 2097.
- (2005) J. Org. Chem. , vol.70 , pp. 2097
- Taillier, C.¹ Gille, B.² Bellosta, V.³ Cossy, J.⁴

21
- 0000096360
- P. L. Creger, J. Am. Chem. Soc. 1970, 92, 1396
- (1970) J. Am. Chem. Soc. , vol.92 , pp. 1396
- Creger, P.L.¹

22
- 15444364346
- P. L. Creger, Org. Synth. 1970, 50, 58.
- (1970) Org. Synth. , vol.50 , pp. 58
- Creger, P.L.¹

23
- 33750283011
- N. Miyaura, T. Ishiyama, H. Sasaki, M. Ishikawa, M. Satoh, A. Suzuki, J. Am. Chem. Soc. 1989, 111, 314
- (1989) J. Am. Chem. Soc. , vol.111 , pp. 314
- Miyaura, N.¹ Ishiyama, T.² Sasaki, H.³ Ishikawa, M.⁴ Satoh, M.⁵ Suzuki, A.⁶

24
- 0011806674
- T. Oh-e, N. Miyaura, A. Suzuki, Synlett 1990, 221
- (1990) Synlett , pp. 221
- Oh-E, T.¹ Miyaura, N.² Suzuki, A.³

25
- 85039397112
- T. Watanabe, N. Miyaura, A. Suzuki, Synlett 1992, 207
- (1992) Synlett , pp. 207
- Watanabe, T.¹ Miyaura, N.² Suzuki, A.³

26
- 2042507954
- N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457.
- (1995) Chem. Rev. , vol.95 , pp. 2457
- Miyaura, N.¹ Suzuki, A.²

27
- 33845924251
- A. Fürstner, D. DeSouza, L. Turet, M. D. B. Fenster, L. Parra-Rapado, C. Wirtz, R. Mynott, C. W. Lehmann, Chem. Eur. J. 2007, 13, 115.
- (2007) Chem. Eur. J. , vol.13 , pp. 115
- Fürstner, A.¹ Desouza, D.² Turet, L.³ Fenster, M.D.B.⁴ Parra-Rapado, L.⁵ Wirtz, C.⁶ Mynott, R.⁷ Lehmann, C.W.⁸

28
- 0002727487
- G. Solladié, C. Fréchou, J. Hutt, G. Demailly, Bull. Soc. Chim. Fr. 1987, 827.
- (1987) Bull. Soc. Chim. Fr. , pp. 827
- Solladié, G.¹ Fréchou, C.² Hutt, J.³ Demailly, G.⁴

29
- 34347250683
- C. Drago, L. Caggiano, R. F. W. Jackson, Angew. Chem. 2005, 117, 7387
- (2005) Angew. Chem. , vol.117 , pp. 7387
- Drago, C.¹ Caggiano, L.² Jackson, R.F.W.³

30
- 27844548710
- Angew. Chem. Int. Ed. 2005, 44, 7221.
- (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 7221

31
- 0000091929
- G. Solladié, G. Demailly, C. Greck, Tetrahedron Lett. 1985, 26, 435
- (1985) Tetrahedron Lett. , vol.26 , pp. 435
- Solladié, G.¹ Demailly, G.² Greck, C.³

32
- 33845375977
- G. Solladié, C. Fréchou, G. Demailly, C. Greck, J. Org. Chem. 1986, 51, 1912
- (1986) J. Org. Chem. , vol.51 , pp. 1912
- Solladié, G.¹ Fréchou, C.² Demailly, G.³ Greck, C.⁴

33
- 0001296747
- M. C. Carreno, J. L. GarciaRuano, A. M. Martin, C. Pedregal, J. H. Rodriguez, A. Rubio, J. Sanchez, G. Solladié, J. Org. Chem. 1990, 55, 2120.
- (1990) J. Org. Chem. , vol.55 , pp. 2120
- Carreno, M.C.¹ Garciaruano, J.L.² Martin, A.M.³ Pedregal, C.⁴ Rodriguez, J.H.⁵ Rubio, A.⁶ Sanchez, J.⁷ Solladié, G.⁸

34
- 38349076159
- For the oxidative functionalization of trisubstituted alkenes, see:, S. Raghavan, T. Sreekanth, Tetrahedron Lett. 2008, 49, 1169; see also
- (2008) Tetrahedron Lett. , vol.49 , pp. 1169
- Raghavan, S.¹ Sreekanth, T.²

35
- 0003531677
- F. Montanari, R. Danieli, H. Hogeveen, G. Maccagnani, Tetrahedron Lett. 1964, 5, 2685
- (1964) Tetrahedron Lett. , vol.5 , pp. 2685
- Montanari, F.¹ Danieli, R.² Hogeveen, H.³ MacCagnani, G.⁴

36
- 0001071070
- D. R. Dalton, V. P. Dutta, D. C. Jones, J. Am. Chem. Soc. 1968, 90, 5498.
- (1968) J. Am. Chem. Soc. , vol.90 , pp. 5498
- Dalton, D.R.¹ Dutta, V.P.² Jones, D.C.³

37
- 0001762455
- W. Markownikoff, Justus Liebigs Ann. Chem. 1870, 153, 256; for a modern interpretation, see
- (1870) Justus Liebigs Ann. Chem. , vol.153 , pp. 256
- Markownikoff, W.¹

38
- 0040454662
- N. Isenberg, M. J. Grdinic, Chem. Educ. 1969, 46, 601.
- (1969) Chem. Educ. , vol.46 , pp. 601
- Isenberg, N.¹ Grdinic, M.J.²

39
- 0000355339
- 2 in a 54.5 % overall yield; see the Supporting Information.
- (1987) J. Org. Chem. , vol.52 , pp. 1236
- Marshall, J.A.¹ Shearer, B.G.² Crooks, S.L.³

40
- 85007950754
- P. J. Stang, M. Hanack, L. R. Subramanian, Synthesis 1982, 85.
- (1982) Synthesis , pp. 85
- Stang, P.J.¹ Hanack, M.² Subramanian, L.R.³

41
- 0000192963
- Y. Oikawa, T. Yoshioka, O. Yonemitsu, Tetrahedron Lett. 1982, 23, 885.
- (1982) Tetrahedron Lett. , vol.23 , pp. 885
- Oikawa, Y.¹ Yoshioka, T.² Yonemitsu, O.³

42
- 0029829555
- A. E. J. DeNooy, A. C. Besemer, H. vanBekkum, Synthesis 1996, 1153.
- (1996) Synthesis , pp. 1153
- Denooy, A.E.J.¹ Besemer, A.C.² Vanbekkum, H.³

43
- 84970543440
- Prenyllithium was prepared by reductive cleavage of phenylprenyl ether with lithium; see:, A. J. Birch, J. E. T. Corrie, G. S. R. SubbaRao, Aust. J. Chem. 1970, 23, 1811.
- (1970) Aust. J. Chem. , vol.23 , pp. 1811
- Birch, A.J.¹ Corrie, J.E.T.² Subbarao, G.S.R.³

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.