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1
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0000733792
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For an isolation and structure determination of the dactomelynes, see: Y. Gopichand, F. J. Schmitz, J. Shelly, A. Rahman, D. van der Helm, J. Org. Chem. 1981, 46, 5192;
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Gopichand, Y.1
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Shelly, J.3
Rahman, A.4
Van Der Helm, D.5
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2
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10744233956
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reisolation
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reisolation: Z. Aydogmus, S. Imre, L. Ersoy, V. Wray, Nat. Prod. Res. 2004, 18, 43.
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Aydogmus, Z.1
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Ersoy, L.3
Wray, V.4
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3
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0000172545
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For the isolation and structure determination of notoryne, see: H. Kikuchi, T. Suzuki, E. Kurosawa, M. Suzuki, Bull. Chem. Soc. Jpn. 1991, 64, 1763.
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Bull. Chem. Soc. Jpn.
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Kikuchi, H.1
Suzuki, T.2
Kurosawa, E.3
Suzuki, M.4
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4
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0003870275
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(Ed.: P. J. Scheuer), Academic Press, New York
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K. L. Erickson in Marine Natural Products, Vol. 5 (Ed.: P. J. Scheuer), Academic Press, New York, 1983, p. 131.
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Marine Natural Products, Vol. 5
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Erickson, K.L.1
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6
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0027461176
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A. D. Wright, G. M. König, R. De Nys, O. Sticher, J. Nat. Prod. 1993, 56, 394.
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J. Nat. Prod.
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Wright, A.D.1
König, G.M.2
De Nys, R.3
Sticher, O.4
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7
-
-
0029099534
-
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For a notable previous total synthesis of the dactomelynes, see: E. Lee, C. M. Park, J. S. Yun, J. Am. Chem. Soc. 1995, 117, 8017.
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Lee, E.1
Park, C.M.2
Yun, J.S.3
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9
-
-
0002736658
-
-
For a summary of the advantages of two-directional synthesis, see: C. S. Poss, S. L. Schreiber, Acc. Chem. Res., 1994, 27, 9.
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(1994)
Acc. Chem. Res.
, vol.27
, pp. 9
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Poss, C.S.1
Schreiber, S.L.2
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10
-
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0028799792
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For an excellent review on desymmetrization and the two-directional synthesis of natural products, see: S. R. Magnuson, Tetrahedron 1995, 51, 2167.
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(1995)
Tetrahedron
, vol.51
, pp. 2167
-
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Magnuson, S.R.1
-
11
-
-
0002050929
-
-
The bis(lactone) 5 has been synthesized in two steps from commercially available materials: M. E. Maier, S. Reuter, Synlett 1995, 1029.
-
(1995)
Synlett
, pp. 1029
-
-
Maier, M.E.1
Reuter, S.2
-
13
-
-
0029145044
-
-
For the formation of endo-glycals using iodotrimethylsilane and hexamethyldisilazane, see: D. Craig, M. W. Pennington, P. Warner, Tetrahedron Lett. 1995, 36, 5815;
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Tetrahedron Lett.
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, pp. 5815
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Craig, D.1
Pennington, M.W.2
Warner, P.3
-
15
-
-
33751005528
-
-
note
-
The anomeric acetates 6 gave the pyrano[3,2-b]pyran 8 in low yield on treatment with iodotrimethylsilane in acetonitrile.
-
-
-
-
16
-
-
0035936738
-
-
J. D. Rainier, S. P. Allwein, J. M. Cox, J. Org. Chem. 2001, 66, 1380.
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J. Org. Chem.
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Rainier, J.D.1
Allwein, S.P.2
Cox, J.M.3
-
17
-
-
33750973007
-
-
note
-
The asymmetric diol was inseparable at this stage and was removed after ozonolysis of 11.
-
-
-
-
18
-
-
33750968135
-
-
note
-
[8].
-
-
-
-
20
-
-
0001653177
-
-
Solvent effects in the reduction of halides and tosylates: S. Krishnamurthy, J. Org. Chem. 1980, 45, 2550.
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(1980)
J. Org. Chem.
, vol.45
, pp. 2550
-
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Krishnamurthy, S.1
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21
-
-
0027997412
-
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S. V. Ley, J. Norman, W. P. Griffith, S. P. Marsden, Synthesis 1994, 639.
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(1994)
Synthesis
, pp. 639
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Ley, S.V.1
Norman, J.2
Griffith, W.P.3
Marsden, S.P.4
-
22
-
-
0001539666
-
-
Y. Yamakado, M. Ishiguro, N. Ikeda, H. Yamamoto, J. Am. Chem. Soc. 1981, 103, 5568.
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J. Am. Chem. Soc.
, vol.103
, pp. 5568
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-
Yamakado, Y.1
Ishiguro, M.2
Ikeda, N.3
Yamamoto, H.4
-
24
-
-
0020766660
-
-
Bromination of the bis(triflate) 20 cannot occur from the ground state, O-inside conformation, and will be further slowed by the β-oxygen effect, see: S. S. Shaik, J. Am. Chem. Soc. 1983, 105, 4359.
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(1983)
J. Am. Chem. Soc.
, vol.105
, pp. 4359
-
-
Shaik, S.S.1
-
25
-
-
33750987260
-
-
For discussion of the conformational preferences of pyrano[3,2-b]pyrans and related systems, see: R. W. Hoffmann, I. Münster, Ann. Chem. 1997, 1143;
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(1997)
Ann. Chem.
, pp. 1143
-
-
Hoffmann, R.W.1
Münster, I.2
-
27
-
-
0034708657
-
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M. Grabarnik, N. G. Lemcoff, R. Madar, S. Abramson, S. Weinman, B. Fuchs, J. Org. Chem. 2000, 65, 1636.
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J. Org. Chem.
, vol.65
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-
Grabarnik, M.1
Lemcoff, N.G.2
Madar, R.3
Abramson, S.4
Weinman, S.5
Fuchs, B.6
-
28
-
-
33750974706
-
-
note
-
The stereochemistry of the dibromide was established by analysis of the coupling constants (see the Supporting Information).
-
-
-
-
29
-
-
33751006676
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-
note
-
The diol 10 contained an inseparable impurity which was removed after chlorination of 23.
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-
-
-
30
-
-
33750971391
-
-
note
-
1H NMR COSY experiments. The origin of the regioselectivity of the Wittig reaction may be steric in nature because of the larger size of an OTES group with respect to a chlorine atom.
-
-
-
-
32
-
-
33750984463
-
-
note
-
The enyne 4 was isolated as an inseparable 8:1 mixture of E and Z isomers.
-
-
-
-
33
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-
33751019605
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-
For an excellent review regarding recent misassigned natural products, see: K. C. Nicolaou, S. A. Snyder, Angew. Chem. 2005, 117, 2086;
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(2005)
Angew. Chem.
, vol.117
, pp. 2086
-
-
Nicolaou, K.C.1
Snyder, S.A.2
-
35
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33751009044
-
-
note
-
13C NMR chemical shifts for 74 synthetic pyrano[3,2-b]pyran and 27 synthetic 2,2′-bifuranyl compounds.
-
-
-
-
36
-
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33750987025
-
-
note
-
[2].
-
-
-
-
37
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-
33751008304
-
-
PhD Thesis, La Trobe University (Australia)
-
15 halogenated 2,2′-bifuranyl natural products had been reported. A 2,2′-bifuranyl structure for elatenyne was considered less likely than the corresponding pyrano[3,2-b]pyran: J. G. Hall, PhD Thesis, La Trobe University (Australia), 1984.
-
(1984)
-
-
Hall, J.G.1
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38
-
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33750985624
-
-
note
-
Unlike a number of pyrano[3,2-b]pyrans we synthesized, neither elatenyne nor the enyne from L. majuscula are crystalline which may be partly because of the extra degree of freedom around the central C-C bond in 2,2′-bifuranyl units.
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