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Synlett

Volumn , Issue 13, 2009, Pages 2129-2132

Stereoselective total synthesis of stagonolide C and formal total synthesis of modiolide A

(4) Mohapatra, Debendra K a Dash, Uttam a Naidu, P Ramesh a Yadav, J S a

a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY (India)

Author keywords

Decanolide; Modiolide A; Ring closing metathesis; Sharpless asymmetric epoxidation; Stagonolide C

Indexed keywords

LACTONE DERIVATIVE; MODIOLIDE A; STAGONOLIDE C; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; REACTION ANALYSIS; RING CLOSING METATHESIS; SHARPLESS EPOXIDATION; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 68949163948 PISSN: 09365214 EISSN: 14372096 Source Type: Journal
DOI: 10.1055/s-0029-1217556 Document Type: Article

Times cited : (41)

References (47)

1
- 0030468778
- For reviews on synthetic, biosynthetic, and pharmacological aspects of decanolides, see: a
- For reviews on synthetic, biosynthetic, and pharmacological aspects of decanolides, see: (a) Dräger, G.; Kirschning, A.; Thiericke, R.; Zerlin, M. Nat. Prod. Rep. 1996, 13, 365.
- (1996) Nat. Prod. Rep , vol.13 , pp. 365
- Dräger, G.¹ Kirschning, A.² Thiericke, R.³ Zerlin, M.⁴

2
- 36448957637
- (b) Ferraz, H. M. C.; Bombonato, F. I.; Longo, L. S. Jr. Synthesis 2007, 3261.
- (2007) Synthesis , pp. 3261
- Ferraz, H.M.C.¹ Bombonato, F.I.² Longo Jr., L.S.³

3
- 38749148766
- (c) Riatto, V. B.; Pilli, R. A.; Victor, M. M. Tetrahedron 2008, 64, 2279.
- (2008) Tetrahedron , vol.64 , pp. 2279
- Riatto, V.B.¹ Pilli, R.A.² Victor, M.M.³

4
- 34948818119
- Yuzikhin, O.; Mitina, G.; Berestetskiy, A. J. Agric. Food Chem. 2007, 55, 7707.
- (2007) J. Agric. Food Chem , vol.55 , pp. 7707
- Yuzikhin, O.¹ Mitina, G.² Berestetskiy, A.³

5
- 39049087094
- (a) Evidente, A.; Cimmino, A.; Berestetskiy, A.; Mitina, G.; Andolfi, A.; Motta, A. J. Nat. Prod. 2008, 71, 31.
- (2008) J. Nat. Prod , vol.71 , pp. 31
- Evidente, A.¹ Cimmino, A.² Berestetskiy, A.³ Mitina, G.⁴ Andolfi, A.⁵ Motta, A.⁶

6
- 58149168970
- (b) Evidente, A.; Cimmino, A.; Berestetskiy, A.; Andolfi, A.; Motta, A. J. Nat. Prod. 2008, 71, 1897.
- (2008) J. Nat. Prod , vol.71 , pp. 1897
- Evidente, A.¹ Cimmino, A.² Berestetskiy, A.³ Andolfi, A.⁴ Motta, A.⁵

7
- 0037352295
- (c) Tsuda, M.; Mugishima, T.; Komatsu, K.; Sone, T.; Tanaka, M.; Mikami, Y.; Kobayashi, J. J. Nat. Prod. 2003, 66, 412.
- (2003) J. Nat. Prod , vol.66 , pp. 412
- Tsuda, M.¹ Mugishima, T.² Komatsu, K.³ Sone, T.⁴ Tanaka, M.⁵ Mikami, Y.⁶ Kobayashi, J.⁷

8
- 33749026617
- (a) Gradillas, A.; Pérez-Castells, J. Angew. Chem. Int. Ed. 2006, 45, 6086.
- (2006) Angew. Chem. Int. Ed , vol.45 , pp. 6086
- Gradillas, A.¹ Pérez-Castells, J.²

9
- 2942589152
- (b) Deiters, A.; Martin, S. F. Chem. Rev. 2004, 104, 2199.
- (2004) Chem. Rev , vol.104 , pp. 2199
- Deiters, A.¹ Martin, S.F.²

10
- 3343012187
- (c) Grubbs, R. H. Tetrahedron 2004, 60, 7117.
- (2004) Tetrahedron , vol.60 , pp. 7117
- Grubbs, R.H.¹

11
- 0038373087
- (d) Prunet, J. Angew. Chem. Int. Ed. 2003, 42, 2826.
- (2003) Angew. Chem. Int. Ed , vol.42 , pp. 2826
- Prunet, J.¹

12
- 1442360753
- Grubbs, R. H, Ed, Wiley-VCH: Weinheim
- (e) Love, J. A. In Handbook of Metathesis; Grubbs, R. H., Ed.; Wiley-VCH: Weinheim, 2003, 296.
- (2003) Handbook of Metathesis , pp. 296
- Love, J.A.¹

13
- 0034746687
- (f) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18.
- (2001) Acc. Chem. Res , vol.34 , pp. 18
- Trnka, T.M.¹ Grubbs, R.H.²

14
- 0001399412
- (g) Fürstner, A. Angew. Chem. Int. Ed. 2000, 39, 3012.
- (2000) Angew. Chem. Int. Ed , vol.39 , pp. 3012
- Fürstner, A.¹

15
- 0034674322
- (h) Maier, M. E. Angew. Chem. Int. Ed. 2000, 39, 2073.
- (2000) Angew. Chem. Int. Ed , vol.39 , pp. 2073
- Maier, M.E.¹

16
- 0032580376
- (i) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413.
- (1998) Tetrahedron , vol.54 , pp. 4413
- Grubbs, R.H.¹ Chang, S.²

17
- 28244440935
- (j) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371.
- (1998) J. Chem. Soc., Perkin Trans. 1 , pp. 371
- Armstrong, S.K.¹

18
- 0033617388
- (k) Gerlach, K.; Quitschalle, M.; Kalesse, M. Tetrahedron Lett. 1999, 40, 3553.
- (1999) Tetrahedron Lett , vol.40 , pp. 3553
- Gerlach, K.¹ Quitschalle, M.² Kalesse, M.³

19
- 0035813926
- (l) Nevalainen, M.; Koskinen, A. M. P. Angew. Chem. Int. Ed. 2001, 40, 4060.
- (2001) Angew. Chem. Int. Ed , vol.40 , pp. 4060
- Nevalainen, M.¹ Koskinen, A.M.P.²

20
- 62949245627
- Perepogu, A. K.; Raman, D.; Murty, U. S. N.; Rao, V. J. Bioorg. Chem. 2009, 37, 46.
- (2009) Bioorg. Chem , vol.37 , pp. 46
- Perepogu, A.K.¹ Raman, D.² Murty, U.S.N.³ Rao, V.J.⁴

21
- 68949129682
- submitted
- (a) Mohapatra, D. K.; Sahoo, G.; Ramesh, D. K.; Sastry, G. N. Chem. Eur. J. 2009, submitted.
- (2009) Chem. Eur. J
- Mohapatra, D.K.¹ Sahoo, G.² Ramesh, D.K.³ Sastry, G.N.⁴

22
- 34548250514
- (b) Ghosh, S.; Rao, R. V. Tetrahedron Lett. 2007, 48, 6937.
- (2007) Tetrahedron Lett , vol.48 , pp. 6937
- Ghosh, S.¹ Rao, R.V.²

23
- 33847620782
- (c) Mohapatra, D. K.; Ramesh, D. K.; Giardello, M. A.; Chorghade, M. S.; Gurjar, M. K.; Grubbs, R. H. Tetrahedron Lett. 2007, 48, 2621.
- (2007) Tetrahedron Lett , vol.48 , pp. 2621
- Mohapatra, D.K.¹ Ramesh, D.K.² Giardello, M.A.³ Chorghade, M.S.⁴ Gurjar, M.K.⁵ Grubbs, R.H.⁶

24
- 34250364465
- (d) Fürstnet, A.; Nagano, T.; Müller, C.; Seidel, G.; Müller, O. Chem. Eur. J. 2007, 13, 1452.
- (2007) Chem. Eur. J , vol.13 , pp. 1452
- Fürstnet, A.¹ Nagano, T.² Müller, C.³ Seidel, G.⁴ Müller, O.⁵

25
- 33845194412
- (e) Prasad, K. R.; Penchalaiah, K.; Choudhary, A.; Anbarsan, P. Tetrahedron Lett. 2007, 48, 309.
- (2007) Tetrahedron Lett , vol.48 , pp. 309
- Prasad, K.R.¹ Penchalaiah, K.² Choudhary, A.³ Anbarsan, P.⁴

26
- 33646697525
- (f) Sharma, G. V. M.; Cherukupalli, G. R. Tetrahedron: Asymmetry 2006, 17, 1081.
- (2006) Tetrahedron: Asymmetry , vol.17 , pp. 1081
- Sharma, G.V.M.¹ Cherukupalli, G.R.²

27
- 28044436733
- (g) Garćia-Fortanet, J.; Murga, J.; Falomir, E.; Carda, M.; Marco, J. A. J. Org. Chem. 2005, 70, 9822.
- (2005) J. Org. Chem , vol.70 , pp. 9822
- Garćia-Fortanet, J.¹ Murga, J.² Falomir, E.³ Carda, M.⁴ Marco, J.A.⁵

28
- 34447633382
- (h) Matsuda, M.; Yamazaki, T.; Fuhshuku, K.; Sugai, T. Tetrahedron 2007, 63, 8752.
- (2007) Tetrahedron , vol.63 , pp. 8752
- Matsuda, M.¹ Yamazaki, T.² Fuhshuku, K.³ Sugai, T.⁴

29
- 2342574741
- (i) Gurjar, M. K.; Karmakar, S.; Mohapatra, D. K. Tetrahedron Lett. 2004, 45, 4525.
- (2004) Tetrahedron Lett , vol.45 , pp. 4525
- Gurjar, M.K.¹ Karmakar, S.² Mohapatra, D.K.³

30
- 33644679006
- (j) Salaskar, A.; Sharma, A.; Chattopadhyay, S. Tetrahedron: Asymmetry 2006, 17, 325.
- (2006) Tetrahedron: Asymmetry , vol.17 , pp. 325
- Salaskar, A.¹ Sharma, A.² Chattopadhyay, S.³

31
- 33748281739
- (k) Boruwa, J.; Gogoi, N.; Barua, N. C. Org. Biomol. Chem. 2006, 4, 3521.
- (2006) Org. Biomol. Chem , vol.4 , pp. 3521
- Boruwa, J.¹ Gogoi, N.² Barua, N.C.³

32
- 17844363491
- (l) Nanda, S. Tetrahedron Lett. 2005, 46, 3661.
- (2005) Tetrahedron Lett , vol.46 , pp. 3661
- Nanda, S.¹

33
- 0034685301
- (m) Arai, M.; Morita, N.; Aoyagi, S.; Kibayashi, C. Tetrahedron Lett. 2000, 41, 1199.
- (2000) Tetrahedron Lett , vol.41 , pp. 1199
- Arai, M.¹ Morita, N.² Aoyagi, S.³ Kibayashi, C.⁴

34
- 0021925374
- (a) Guindon, Y.; Yoakim, C.; Bernstein, M. A.; Morton, H. E. Tetrahedron Lett. 1985, 26, 1185.
- (1985) Tetrahedron Lett , vol.26 , pp. 1185
- Guindon, Y.¹ Yoakim, C.² Bernstein, M.A.³ Morton, H.E.⁴

35
- 0037025953
- and references therein
- (b) Takemura, T.; Nishi, Y.; Takahashi, S.; Kobayashi, J.; Nakata, T. Tetrahedron 2002, 58, 6359; and references therein.
- (2002) Tetrahedron , vol.58 , pp. 6359
- Takemura, T.¹ Nishi, Y.² Takahashi, S.³ Kobayashi, J.⁴ Nakata, T.⁵

36
- 18844410382
- Gao, Y.; hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765.
- (1987) J. Am. Chem. Soc , vol.109 , pp. 5765
- Gao, Y.¹ hanson, R.M.² Klunder, J.M.³ Ko, S.Y.⁴ Masamune, H.⁵ Sharpless, K.B.⁶

37
- 32244442039
- Reddy, L. V. R.; Sagar, R.; Shaw, A. K. Tetrahedron Lett. 2006, 47, 1753.
- (2006) Tetrahedron Lett , vol.47 , pp. 1753
- Reddy, L.V.R.¹ Sagar, R.² Shaw, A.K.³

38
- 0028798176
- Rama Rao, A. V.; Murthy, V. S.; Sharma, G. V. M. Tetrahedron Lett. 1995, 36, 139.
- (1995) Tetrahedron Lett , vol.36 , pp. 139
- Rama Rao, A.V.¹ Murthy, V.S.² Sharma, G.V.M.³

39
- 68949087199
- Analytical and spectral data of 17: [α]D 27 -30.4 (c 1.8, CHCl3, IR (KBr, 3456, 2922, 2853, 1616, 1513, 1247 cm-1; 1H NMR (300 MHz, CDCl3, δ, 7.16 (d, J, 9.0 Hz, 2 H, 6.73 (d, J, 9.0 Hz, 2 H, 5.80-5.68 (m, 1 H, 5.23-5.14 (m, 2 H, 4.51-4.48 (m, 1 H, 4.48 (d, J, 11.3 Hz, 1 H, 4.19 (d, J, 11.3 Hz, 1 H, 4.01-3.94 (m, 1 H, 3.73 (s, 3 H, 1.67-1.50 (m, 2 H, 1.07 (d, J, 6.8 Hz, 3 H, 13C NMR (75 MHz, CDCl3, δ, 159.2, 138.1, 129.4, 128.6, 117.1, 113.8, 77.6, 69.9, 64.6, 55.2, 43.5, 23.3; MS (ESI, m/z, 237 [M, H, 259 [M, Na, HRMS ESI, m/z [M, H, calcd for C14H20O3Na: 259.1310; found: 259.1318
- 3Na: 259.1310; found: 259.1318.

40
- 33751257490
- and references therein
- Ravelo, J. L.; Rodriguez, C. M.; Martin, V. S. J. Organomet. Chem. 2006, 691, 5326; and references therein.
- (2006) J. Organomet. Chem , vol.691 , pp. 5326
- Ravelo, J.L.¹ Rodriguez, C.M.² Martin, V.S.³

41
- 0027988788
- Frigerio, M.; Santagostino, M. Tetrahedron Lett. 1994, 35, 8019.
- (1994) Tetrahedron Lett , vol.35 , pp. 8019
- Frigerio, M.¹ Santagostino, M.²

42
- 33748664603
- (a) Balkrishna, S. B.; Childers, W. E. Jr.; Pinnick, H. W. Tetrahedron 1981, 37, 2091.
- (1981) Tetrahedron , vol.37 , pp. 2091
- Balkrishna, S.B.¹ Childers Jr., W.E.² Pinnick, H.W.³

43
- 33845374026
- (b) Dalcanale, E.; Montanari, F. J. Org. Chem. 1986, 51, 567.
- (1986) J. Org. Chem , vol.51 , pp. 567
- Dalcanale, E.¹ Montanari, F.²

44
- 68949143769
- Analytical and spectral data of 18: [α]D 27 -30.5 (c 2.7, CHCl3, IR (KBr, 3426, 2929, 2865, 1709, 1610, 1513, 1455, 1250 cm-1; 1H NMR (300 MHz, CDCl3, δ, 7.16 (d, J, 8.7 Hz, 2 H, 6.8 (d, J, 8.7 Hz, 2 H, 5.77-5.65 (m, 1 H, 5.25-5.2 (m, 2 H, 4.51 (d, J, 11.4 Hz, 1 H, 4.25 (d, J, 11.4 Hz, 1 H, 3.77 (s, 3 H, 3.77-3.70 (m, 1 H, 2.41 (t, J, 7.3 Hz, 2 H, 1.91-1.78 (m, 2 H, 13C NMR (75 MHz, CDCl3, δ, 179.4, 159.0, 138.0, 130.2, 129.3, 117.6, 113.6, 78.7, 69.7, 55.1, 30.0, 29.9; MS (ESI, m/z, 273 [M, Na, HRMS ESI, m/z [M, H, calcd for C 14H18O4Na: 273.1102; found: 273.1101
- 4Na: 273.1102; found: 273.1101.

45
- 68949143768
- Analytical and spectral data of 15: [α]D 27 -55.3 (c 1.9, CHCl3, IR (KBr, 2923, 2853, 1729,1613, 1513, 1377, 1248 cm-1; 1H NMR (300 MHz, CDCl3, δ, 7.28-7.24 (m, 4 H, 6.91-6.85 (m, 4 H, 5.80-5.68 (m, 2 H, 5.29-5.13 (m, 5 H, 4.54 (d, J, 11.5 Hz, 1 H, 4.51 (d, J, 11.3 Hz, 1 H, 4.27 (d, J, 11.3 Hz, 1 H, 4.21 (d, J, 11.5 Hz, 1 H, 3.82 (s, 3 H, 3.80 (s, 3 H, 3.80-3.72 (m, 2 H, 2.41-2.18 (m, 2 H, 1.96-1.67 (m, 4 H, 1.21 (d, J, 6.2 Hz, 3 H, 13C NMR (75 MHz, CDCl3, δ, 172.8, 159.0, 138.5, 138.3, 130.5, 130.3, 129.6, 129.3, 117.5, 117.0, 113.7, 79.1, 76.3, 69.9, 69.8, 67.6, 55.2, 42.2, 30.5, 30.4, 20.5; MS (ESI, m/z, 491 [M, Na, HRMS ESI, m/z [M, H, calcd for C28H36O6Na: 491.2409; found: 491.2413
- 6Na: 491.2409; found: 491.2413.

46
- 68949104547
- +.
- +.

47
- 68949085997
- Analytical and spectral data of 33: [α]D 27 +14.7 (c 1.4, EtOH, IR (KBr, 2931, 2859, 1731, 1645, 1461, 1370, 1248 cm-1; 1H NMR (300 MHz, CDCl3, δ, 5.45 (dd, J, 15.8, 9.0 Hz, 1 H, 5.30 (dd, J, 15.8, 8.6 Hz, 1 H, 5.14-5.03 (m, 1 H, 4.08-3.97 (m, 2 H, 2.26-2.20 (m, 1 H, 2.05-1.96 (m, 2 H, 1.95-1.84 (m, 1 H, 1.78-1.71 (m, 2 H, 1.18 (d, J, 6.6 Hz, 3 H, 0.86 (s, 9 H, 0.85 (s, 9 H, 0.04 (s, 6 H, 0.02 (s, 6 H, 13C NMR (75 MHz, CDCl3, δ, 174.4, 135.1, 132.4, 75.3, 73.0, 67.5, 44.8, 35.5, 31.5, 25.7, 21.4, 18.1, 4.3, 4.4, 4.7; MS (ESI, m/z, 429 [M, H, HRMS ESI, m/z [M, H, calcd for C22H44O4NaSi2: 451.2675; found: 451.2675
- 2: 451.2675; found: 451.2675.

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