References
1
Seto H.
Koyama M.
Ogino H.
Tsuruoka T.
Inoue S.
Otake N.
Tetrahedron Lett.
1983,
24:
1805
2
Garner P.
Yoo JU.
Sarabu R.
Kennedy VO.
Yongs WJ.
Tetrahedron
1998,
54:
9303
3a
Casiraghi G.
Colombo L.
Rassu G.
Spanu P.
J. Chem. Soc., Chem. Commun.
1991,
603
3b
Casiraghi G.
Colombo L.
Rassu G.
Spanu P.
J. Org. Chem.
1991,
56:
6523
4a
Czernecki S.
Horns S.
Valéry JM.
J. Org. Chem.
1995,
60:
650
4b
Czernecki S.
Franco S.
Horns S.
Valéry JM.
Tetrahedron Lett.
1996,
37:
4003
5
Hara K.
Fujimoto H.
Sato K.-I.
Hashimoto H.
Yoshimura J.
Carbohydr. Res.
1987,
159:
65
6
Fairbanks AJ.
Sinaӱ P.
Synlett
1994,
3:
277
7
Rauter AP.
Oliveira O.
Canda T.
Leroi E.
Ferreira H.
Ferreira MJ.
Ascenso JA.
J. Carbohydr. Chem.
2002,
21:
257
For reviews concerning RCM reactions, see:
8a
Grubbs RH.
Miller SJ.
Fu GC.
Acc. Chem. Res.
1995,
28:
446
8b
Schuster M.
Blechert S.
Angew. Chem., Int. Ed. Engl.
1997,
36:
2036
8c
Armstrong SK.
J. Chem. Soc., Perkin Trans. 1
1997,
371
8d
Grubbs RH.
Chang S.
Tetrahedron
1998,
54:
4413
8e
Fürstner A.
Angew. Chem. Int. Ed.
2000,
39:
3013
8f
Trnka TM.
Grubbs RH.
Acc. Chem. Res.
2001,
34:
18
For reviews, see:
9a
Roy R.
Das SK.
Chem. Commun.
2000,
519
9b
Sinou D.
Bedjeguelal K.
J. Carbohydr. Chem.
2001,
20:
335
10a
Holt DJ.
Barker WD.
Jenkins PR.
Davies DL.
Garratt S.
Fawcett J.
Russell DR.
Ghosh S.
Angew. Chem. Int. Ed.
1998,
37:
3298
10b
Dirat O.
Vidal T.
Langlois Y.
Tetrahedron Lett.
1999,
40:
4801
10c
Holt DJ.
Barker WD.
Jenkins PR.
Panda J.
Ghosh S.
J. Org. Chem.
2000,
65:
482
11
Carey FA.
Frank WC.
J. Org. Chem.
1982,
47:
3548
12 Spectral data for 3: 1H NMR (250 MHz, CDCl3): δ = 3.43 (s, 3 H, OCH3), 3.75 (m, 2 H, H-5, H-6), 3.95 (m, 2 H, H-2, CH2), 4.28 (m, 2 H, H-6′, CH2), 4.83 (d, 1 H, H-1, J = 3.8 Hz), 5.27 (m, 2 H, CH2=), 5.60 (s, 1 H, CH), 5.95 (m, 1 H, CH=), 7.35 (m, 3 H, Ph), 7.53 (m, 2 H, Ph). 13C NMR (63 MHz, CDCl3): δ = 55.7 (OCH3), 66.0 (C5), 69.8 (C6), 72.0 (CH2), 77.0 (C2), 79.0 (C4), 100.0 (C1), 101.9 (CH), 105.4 (CH2=), 118.3 (CH2=), 126.7, 128.7, 129.5 (Ph), 134.8 (CH=). [α]D
20 +70 (c 1, CH2Cl2). MS (NH3, DCI): 336 [M + 18]+.
13 Spectral data for 7: 1H NMR (250 MHz, CDCl3): δ = 3.44 (s, 6 H, OCH3), 3.73 (m, 4 H, H-5, H-6), 3.95 (m, 4 H, H-2, H-4), 4.26 (m, 4 H, CH2), 4.29 (m, 2 H, H-6), 4.85 (d, 2 H, H-1, J = 3.8 Hz), 5.26 (dd, 4 H, CH2=), 5.60 (s, 2 H, CH), 5.88 (m, 2 H, CH=), 7.39 (m, 6 H, Ph), 7.54 (m, 4 H, Ph). 13C NMR (63 MHz, CDCl3): δ = 55.7 (OCH3), 66.0 (C5), 69.8 (C6), 70.8 (CH2), 77.3 (C2), 78.9 (C4), 99.9 (C1), 101.8 (CH), 105.5 (CH2=), 126.6, 128.6, 129.5, 130 (Ph), 134.8 (CH=), 139.5 (Cipso).; MS (NH3, DCI): 626 [M + 18]+.
14
Guerra J.
Synlett
2003,
423
15 Spectral data for 8: 1H NMR (250 MHz, CDCl3): δ = 2.06 (s, 3 H, OAc) 2.15 (s, 3 H, OAc), 3.40 (s, 3 H, OCH3), 3.85 (m, 1 H, H-5), 3.98-4.14 (m, 4 H, H-2, H-6, H-7, H-7′), 4.29 (m, 1 H, H-6), 4.81 (d, 1 H, H-1, J = 3.7 Hz), 4.97 (br s, 1 H, H-4), 5.20 (m, 4 H, CH2=), 5.88 (m, 1 H, CH=). 13C NMR (63 MHz, CDCl3): δ = 21.0. 21.1 (CH3), 55.7 (OCH3), 62.9 (C6), 69.6 (C5), 70.0 (C2), 72.0 (C7), 76.8 (C4), 99.1 (C1), 106.5 (CH2=), 134.5 (CH=), 139.2 (C3), 171.1, 169.8 (CO). Optical rotation: [α]D
20 +66 (c 1, CH2Cl2). MS (NH3, DCI): 332 [M + 18]+.
16
Paquette LA.
Schloss JD.
Efremov I.
Fabris F.
Gallo F.
Mendez-Andino J.
Yang J.
Org. Lett.
2000,
2:
1259
17 Spectal data for 9: 1H NMR (250 MHz, CDCl3): δ = 2.09 (s, 3 H, OAc) 2.14 (s, 3 H, OAc), 3.42 (s, 3 H, OCH3), 3.81 (m, 1 H, H-5), 4.18 (m, 2 H, H-6), 4.73 (m, 1 H, H-2), 4.83 (m, 3 H, H-1, CH2), 5.42 (dd, 1 H, H-4, J = 2.2 Hz, J = 9.7 Hz), 5.60 (bs, 1 H, CH=). 13C NMR (63 MHz, CDCl3): δ = 21.0. 21.1 (CH3), 55.8 (OCH3), 62.8 (C6), 67.7 (C4), 68.9 (C5), 77.7 (C7), 83.7 (C2), 99.7 (C1), 119.2 (CH=), 133.5 (C3), 171.1, 169.9 (CO). [α]D
20 +204 (c 1, CH2Cl2). MS (NH3, DCI): 304 [M + 18]+.
18 Spectral data for 10: 1H NMR (250 MHz, CDCl3): δ = 1.6 (br s, 1 H, OH), 2.09 (s, 3 H, OAc) 2.12 (s, 3 H, OAc), 3.39 (s, 3 H, OCH3), 3.60 (dd, 1 H, H-7), 3.92 (m, 1 H, H-5), 4.10 (d, 1 H, H-2, J = 5.0 Hz), 4.27 (m, 3 H, H-6, H-7′), 4.48 (br s, 1 H, OH), 4.62 (m, 1 H, H-8), 4.73 (d, 1 H, H-1, J = 5.3 Hz), 4.98 (d, 1 H, H-4, J = 10.5 Hz). 13C NMR (63 MHz, CDCl3): δ = 21.1, 21.1 (CH3), 56.1 (OCH3), 62.9 (C6), 64.7 (C5), 72.7 (C8), 74 (C7), 74.3 (C4), 78.1 (C3), 83.6 (C2), 98.8 (C1), 173.2, 171.1 (CO). [α]D
20 +108 (c 1, CH2Cl2).
19
Paquette LA.
Hartung RE.
France DJ.
Org. Lett.
2003,
6:
869
20 Spectral data for 11: 1H NMR (250 MHz, CDCl3): δ = 2.06 (s, 3 H, OAc) 2.11 (s, 3 H, OAc), 3.37 (s, 3 H, OCH3), 3.82 (m, 1 H, H-5), 3.97-4.12 (m, 3 H, H-6, H-7), 4.36 (d, 1 H, H-2, J = 5.3 Hz), 4.54 (dd, 1 H, H-7′, J = 5.8 Hz, J = 10.0 Hz), 4.89 (d, 1 H, H-1, J = 5.3 Hz), 5.25 (dd, 1 H, H-8, J = 6.0 Hz, J = 1.8 Hz), 5.42 (d, 1 H, H-4, J = 10.5 Hz). 13C NMR (63 MHz, CDCl3): δ = 20.5, 20.2 (CH3), 55.4 (OCH3), 61.8 (C6), 64.1 (C5), 67.4 (C4), 75.4 (C7), 79.3 (C2), 80.4 (C8), 98.9 (C1), 153.0 (CO), 168.7, 170.4 (CO). [α]D
20 +67 (c 1.2, CH2Cl2). MS (NH3, DCI): 364 [M + 18]+. IR 1817, 1750 cm-1 (CO).
21
Anelli PL.
Biffi C.
Montanari F.
Quici S.
J. Org. Chem.
1987,
52:
2559
22 Spectral data for 12: 1H NMR (250 MHz, CDCl3): δ = 2.10 (s, 3 H, OAc) 2.19 (s, 3 H, OAc), 3.40 (s, 3 H, OCH3), 4.00 (m, 1 H, H-5), 4.18-4.30 (m, 5 H, H-2, H-6, H-6′, H-7, H-7′), 4.88 (d, 1 H, H-1, J = 5.5 Hz), 4.92 (br s, 1 H, H-4). 13C NMR (63 MHz, CDCl3): δ = 21.4 (CH3), 56.3 (OCH3), 63.0 (C6), 66.0 (C5), 70.6 (C7), 72.5 (C3), 76.6 (C4), 82.0 (C2), 99.1 (C1), 171.3, 175.0 (CO), 207.7 (CO). [α]D
20 +17 (c 0.3, CH2Cl2). MS (NH3, DCI): 336 [M + 18]+.
23 The crystal struture has been deposited at the Cambridge Crystallographic Center and allocated the deposition number: CCDC 224358.
24 Spectral data for 13: 1H NMR (250 MHz, CDCl3): δ = 2.11 (s, 3 H, OAc), 2.53 (s, 1 H, OH), 2.95 (s, 1 H, OH), 3.52 (s, 3 H, OCH3), 3.82 (m, 2 H, H-4, H-5), 3.89 (d, 1 H, H-7, J = 10.3 Hz), 4.02 (d, 1 H, H-2, J = 5.5 Hz), 4.18 (dd, 1 H, H-8, J = 4.8 Hz, J = 12.2 Hz), 4.36 (m, 3 H, 2 H-6, H-7′), 4.53 (d, 1 H, OH, J = 12.2 Hz), 4.86 (d, 1 H, H-1, J = 5.3 Hz). MS (NH3, DCI): 296 [M + 18]+.
