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2. (a) Zhou, Z; Larouche, D.; Bennett, S.M. Tetrahedron 1995, 51, 11623-11644.
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3. For a review on the conversion of carbohydrates to functionalized carbocycles see: Ferrier, R.J.; Midleton, S. Chem. Rev. 1993, 93, 2779-2831.
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9
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0028218744
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2 mediated transformations of carbohydrates to carbocycles via an intramolecular coupling of an aldehyde carbonyl with an α,β - unsaturated ester see: (a) Enholm, E. J. ; Trivellas, A. Tetrahedron Lett. 1994, 35, 1627-1628.
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Enholm, E.J.1
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0030570848
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(c) Grové, J.J.C.; Holzapfel, C.W.; Williams, D.B.G.; Tetrahedron Lett. 1996, 37, 5817-5820.
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Grové, J.J.C.1
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(d) Chiara, J.L.; Martïnez, S.; Bernabé, M. J. Org. Chem., 1996, 61, 6488.
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Chiara, J.L.1
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13
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0000973977
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3SnH mediated radical cyclizations of ωbromo-α,β-unsaturated ethyl esters, derived from D-ribonolactone, have been reported in the literature. See: Wilcox, C.S.; Thomasco, L.M. J. Org. Chem. 1985, 50, 546-547.
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Wilcox, C.S.1
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33847086035
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2 reduction of alkyl halides to the corresponding alkanes was first demonstrated by Kagan. See: (a) Girard, P.; Namy, J.L.; Kagan, H.B. J. Am. Chem. Soc. 1980, 102, 2693 - 2698.
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Girard, P.1
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(b) Kagan, H.B.; Namy, J.L.; Girard, P. Tetrahedron 1981, 37, Suppl. 1, 175-180.
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Kagan, H.B.1
Namy, J.L.2
Girard, P.3
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16
-
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0011472960
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-
2 reactions of unsaturated halides see references 1a and 1c and references therein
-
2 reactions of unsaturated halides see references 1a and 1c and references therein.
-
-
-
-
17
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0000013173
-
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8. (a) Hough, L.; Jones, J. K. N. and Mitchell, D. L. Can. J. Chem. 1958, 36, 1720-1728.
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Hough, L.1
Jones, J.K.N.2
Mitchell, D.L.3
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19
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0002153681
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9. (a) Hanessian, S.; Ponpipon, M. M. and Lavallee, P. Carbohydrate Research. 1972, 24, 45-56;
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Hanessian, S.1
Ponpipon, M.M.2
Lavallee, P.3
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21
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0011382263
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Commercially available from Aldrich
-
10. Commercially available from Aldrich.
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-
-
-
22
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0011429302
-
-
The purification of the 4a and 4b was complicated by the presence of tetrahydrofuran side products (formed by an intramolecular 1,4 - addition of the hydroxyl group onto the α, β-unsaturated ester)
-
11. The purification of the 4a and 4b was complicated by the presence of tetrahydrofuran side products (formed by an intramolecular 1,4 - addition of the hydroxyl group onto the α, β-unsaturated ester).
-
-
-
-
24
-
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0017998510
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13. Höfle, G.; Steglich, W.; Vorbrüggen, H.; Angew. Chem. Int. Ed. Engl. 1978, 17, 569-583.
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Höfle, G.1
Steglich, W.2
Vorbrüggen, H.3
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25
-
-
0011382381
-
-
13C NMR, FTIR, MS) are in agreement with the proposed structures. Yields refer to isolated yields of pure products
-
13C NMR, FTIR, MS) are in agreement with the proposed structures. Yields refer to isolated yields of pure products.
-
-
-
-
26
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0037629474
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2 see : (a) Molander, G.A.; La Belle, B.E.; Hahn, G. J. Org. Chem. 1986, 51, 5259-5264.
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Molander, G.A.1
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Hahn, G.3
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27
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0000272655
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(b) Otsubo, K.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1987, 28, 4437-4440.
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Otsubo, K.1
Inanaga, J.2
Yamaguchi, M.3
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28
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37049075800
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(c) Kang, S.K.; Kim, S.G.; Park, D.C.; Lee, J.S.; Yoo, W.J., Pak, C.S. J.C.S., Perkin Trans I 1993, 9-10.
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Kang, S.K.1
Kim, S.G.2
Park, D.C.3
Lee, J.S.4
Yoo, W.J.5
Pak, C.S.6
-
29
-
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0011382382
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-
note
-
4 and concd. The crude products were purified by flash column chromatography or by radial chromatography [Harrison Research Chromatotron, silica gel or adsorbosil plates] using a mixture of EtOAc and hexanes.
-
-
-
-
30
-
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0011383211
-
-
3SnH reactions
-
3SnH reactions.
-
-
-
-
31
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0011440260
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The stereochemistry of the cyclization products was determined with the help of nOe experiments
-
18. The stereochemistry of the cyclization products was determined with the help of nOe experiments.
-
-
-
-
32
-
-
0011383654
-
-
1H NMR analysis of both the crude and purified products
-
1H NMR analysis of both the crude and purified products.
-
-
-
-
33
-
-
0026016178
-
-
2 radical addition/reductive elimination sequence involving a simple aromatic bromide tethered to an allylic acetate has been reported. See: Inanaga, J.; Ujikawa, O.; Yamaguchi, M. Tetrahedron Lett. 1991, 32, 1737-1740.
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Inanaga, J.1
Ujikawa, O.2
Yamaguchi, M.3
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36
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37049085907
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(c) Crombie, L.; Rainbow, L.J.; J.C.S., Perkin Trans I, 1994, 673-687.
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Crombie, L.1
Rainbow, L.J.2
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37
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37049106529
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(d) Ananthanarayan, T.P.; Gallagher, T.; Magnus, P. J.C.S., Chem. Commun. 1982, 709-710.
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Ananthanarayan, T.P.1
Gallagher, T.2
Magnus, P.3
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