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3
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0026500940
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a) M. R. Prinsep, F. R. Caplan, R. E. Moore, G. M. L. Patterson, C. D. Smith, J. Am. Chem. Soc. 1992, 114, 385;
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(1992)
J. Am. Chem. Soc.
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Prinsep, M.R.1
Caplan, F.R.2
Moore, R.E.3
Patterson, G.M.L.4
Smith, C.D.5
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4
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0029091524
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b) M. R. Prinsep, G. M. L. Patterson, L. K. Larsen, C. D. Smith, Tetrahedron 1995, 51, 10523.
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(1995)
Tetrahedron
, vol.51
, pp. 10523
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Prinsep, M.R.1
Patterson, G.M.L.2
Larsen, L.K.3
Smith, C.D.4
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6
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0001215610
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For seminal work by Eschenmoser and co-workers in this area, see the following reviews: a) A. Eschenmoser, Q. Rev. Chem. Soc. 1970, 24, 366;
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(1970)
Q. Rev. Chem. Soc.
, vol.24
, pp. 366
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Eschenmoser, A.1
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7
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84987288476
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b) M. Roth, E. Dobs, E. Götschi, A. Eschenmoser, Helv. Chim. Acta 1971, 54, 710;
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(1971)
Helv. Chim. Acta
, vol.54
, pp. 710
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Roth, M.1
Dobs, E.2
Götschi, E.3
Eschenmoser, A.4
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8
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33745163521
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see also c) A. P. Johnson, P. Wehrli, R. Fletcher, A. Eschenmoser, Angew. Chem. 1968, 80, 622;
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(1968)
Angew. Chem.
, vol.80
, pp. 622
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Johnson, A.P.1
Wehrli, P.2
Fletcher, R.3
Eschenmoser, A.4
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10
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0015763774
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d) E. Götschi, W. Hunkeler, H.-J. Wild, P. Schneider, W. Fuhrer, J. Gleason, A. Eschenmoser, Angew. Chem. 1973, 85, 950;
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(1973)
Angew. Chem.
, vol.85
, pp. 950
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Götschi, E.1
Hunkeler, W.2
Wild, H.-J.3
Schneider, P.4
Fuhrer, W.5
Gleason, J.6
Eschenmoser, A.7
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12
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84981403311
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e) P. M. Müller, S. Farooq, B. Hardegger, W. S. Salmond, A. Eschenmoser, Angew. Chem. 1973, 85, 954;
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(1973)
Angew. Chem.
, vol.85
, pp. 954
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Müller, P.M.1
Farooq, S.2
Hardegger, B.3
Salmond, W.S.4
Eschenmoser, A.5
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15
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0001074831
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2; 3. lithium diisopropylamide (LDA), THF, -78°C; MeI, hexamethyl phosphoramide (HMPA); 4. LDA, THF, -78°C; TBS-Cl, HMPA.
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(1978)
Tetrahedron
, vol.34
, pp. 1449
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Ravid, U.1
Silverstein, R.M.2
Smith, L.R.3
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16
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85034513524
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note
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For the stereochemical assignment of the quaternary centers, see reference [18].
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17
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33745149667
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Ph.D. Thesis, Harvard University
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Satisfactory spectroscopic data were obtained for all new compounds reported: T. G. Minehan, Ph.D. Thesis, Harvard University, 1998.
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(1998)
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Minehan, T.G.1
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18
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85034510593
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note
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Glycosidation of substrates having less reactive acyl carbonyl groups such as the bis-O-benzoate and the bis-O-para-methoxybenzoate corresponding to 5 was also tested, but the major product in each case was still found to arise from C-C bond formation at the carbonyl carbon atom of the acyl group at C2.
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19
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85034506976
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note
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Base hydrolysis followed by acid work-up yielded three lactones. Treatment with methyllithium or diisobutyl aluminum hydride (DIBAL-H) yielded a ketal or acetal involving the alcohol groups of C9 and C2; attempted hydrolysis of the resultant acetal or ketal failed under a wide range of acidic conditions. Efforts to incorporate "removable" α-quaternary ester protecting groups, for example the α,α-dimethyllevulinoyl group, also met with limited success.
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20
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85034505713
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note
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The product at this stage was a mixture of diastereomers due to the chiral centers at C3, C6, C12, and/or C16.
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21
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85034519406
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note
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Because of its extreme sensitivity to light, purification and manipulation of the cadmium precorphin complex corresponding to 15 presented technical difficulties, resulting in poor overall yields; thus, the nickel-containing substrate was used for further elaboration.
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22
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85034508911
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note
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[4] that this cyclization involves three distinct steps: 1) a slow reaction of the lactam carbonyl with the alkylating reagent, 2) a proton-catalyzed isomerization of the double bonds in the precorphin structure, and 3) an elcctrocyclic ring closure. The addition of methanol serves to release a controlled amount of "catalytic protons" into the reaction medium.
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23
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85034508155
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note
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[3]
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25
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85034514098
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note
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[3]
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26
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0002211812
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M. Node, K. Nishide, K. Sai, K. Ichikawa, K. Fuji, E. Fujita, Chem. Lett. 1979, 97.
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(1979)
Chem. Lett.
, pp. 97
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Node, M.1
Nishide, K.2
Sai, K.3
Ichikawa, K.4
Fuji, K.5
Fujita, E.6
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27
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33745154794
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T. G. Minehan, L. Cook-Blumberg, Y. Kishi, M. R. Prinsep, R. E. Moore, Angew. Chem. 1999, 111, 915;
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(1999)
Angew. Chem.
, vol.111
, pp. 915
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Minehan, T.G.1
Cook-Blumberg, L.2
Kishi, Y.3
Prinsep, M.R.4
Moore, R.E.5
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29
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0001438134
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For previous dioxobacteriochlorin/dioxoisobacteriochlorin syntheses, see a) R. K. Pandey, M. Isaac, I. MacDonald, C J. Medforth, M. O. Senge, T. J. Dougherty, K. M. Smith, J. Org. Chem. 1997, 62, 1463;
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(1997)
J. Org. Chem.
, vol.62
, pp. 1463
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Pandey, R.K.1
Isaac, M.2
MacDonald, I.3
Medforth, C.J.4
Senge, M.O.5
Dougherty, T.J.6
Smith, K.M.7
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31
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33745148788
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J. Micklefield, M. Beckmann, R. L. Mackman, M. H. Block, F. J. Leeper, A. R. Battersby, J. Chem. Soc. Perkin Trans. 1 1997, 2123;
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(1997)
J. Chem. Soc. Perkin Trans. 1
, pp. 2123
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Micklefield, J.1
Beckmann, M.2
Mackman, R.L.3
Block, M.H.4
Leeper, F.J.5
Battersby, A.R.6
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32
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3042868350
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c) F.-P. Montforts, F. Romanowski, J. W. Bats, Angew. Chem. 1989, 101, 471;
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(1989)
Angew. Chem.
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Montforts, F.-P.1
Romanowski, F.2
Bats, J.W.3
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35
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0001515103
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W. G. Salmond, M. A. Barta, J. L. Havens, J. Org. Chem. 1978, 43, 2057.
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(1978)
J. Org. Chem.
, vol.43
, pp. 2057
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Salmond, W.G.1
Barta, M.A.2
Havens, J.L.3
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36
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85034510591
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note
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[2a]
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37
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85034511240
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note
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1H NMR spectra, the synthetic material was once again found not to match the authentic sample.
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