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84988087864
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(a) Mulzer, J.; Pietschman, C.; Schollhorn, B.; Buschmann, J.; Luger, P. Liebigs Ann. Chem. 1995, 1433-1439. For a practical access to multiten grams of 9, see:
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56949086052
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41
-
-
72849114700
-
-
Without the TMS protection, the two C-10 epimers (19a and 19b without the TMS group on C-8 OH) were inseparable on silica gel.
-
Without the TMS protection, the two C-10 epimers (19a and 19b without the TMS group on C-8 OH) were inseparable on silica gel.
-
-
-
-
42
-
-
72849111020
-
-
Essentially no reaction occurred if using Zn or Mg salt of 7. The asymmetric protocol of Carreira see
-
(a) Essentially no reaction occurred if using Zn or Mg salt of 7. The asymmetric protocol of Carreira (see,
-
-
-
-
43
-
-
0041407526
-
-
also failed to yield any products here.
-
(b) Frantz, D. E.; Fassler, R.; Carreira, E. M. J. Am. Chem. Soc. 2000, 122, 1806-1807) also failed to yield any products here.
-
(2000)
J. Am. Chem. Soc.
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-
-
Frantz, D.E.1
Fassler, R.2
Carreira, E.M.3
-
44
-
-
72849140615
-
-
The relative configurations of 19a/b were established through NOEs of their C-8 OH/C-10 OH acetonides.
-
(c) The relative configurations of 19a/b were established through NOEs of their C-8 OH/C-10 OH acetonides.
-
-
-
-
45
-
-
0001408299
-
-
For a literature precedent using a primary amine for such a purpose, see
-
For a literature precedent using a primary amine for such a purpose, see: Czech, B. P.; Barsch, R. A. J. Org. Chem. 1984, 49, 4076-4078.
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Czech, B.P.1
Barsch, R.A.2
-
46
-
-
72849122705
-
-
We are not aware of similar precedents in the literature; such an etherification usually occurs only under basic conditions.
-
We are not aware of similar precedents in the literature; such an etherification usually occurs only under basic conditions.
-
-
-
-
47
-
-
72849106746
-
-
We are not aware of any literature precedents.
-
We are not aware of any literature precedents.
-
-
-
-
48
-
-
0001597804
-
-
Evans, D. A.; Britton, T. C.; Ellman, J. A. Tetrahedron Lett. 1987, 28, 6141-6144.
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49
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15444369904
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Ramachandran, P. V.; Burghardt, T. E.; Reddy, M. V. R. J. Org. Chem. 2005, 70, 2329-2331.
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Ramachandran, P.V.1
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Reddy, M.V.R.3
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50
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33845278140
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Evans, D. A.; Chapman, K. T.; Carreira, E. M. J. Am. Chem. Soc. 1988, 110, 3560-3578.
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0037160423
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(a) Evans, D. A.; Tedrow, J. S.; Shaw, J. T.; Downey, C. W. J. Am. Chem. Soc. 2002, 124, 392-393.
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52
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0037018454
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(b) Evans, D. A.; Downey, C. W.; Shaw, J. T. Org. Lett. 2002, 4, 1127-1130.
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Evans, D.A.1
Downey, C.W.2
Shaw, J.T.3
-
53
-
-
72849127289
-
-
We are not aware of any precedents of application of this protocol to complex enals with an eliminable ethereal group at the allylic position.
-
We are not aware of any precedents of application of this protocol to complex enals with an eliminable ethereal group at the allylic position.
-
-
-
-
54
-
-
0001616071
-
-
For Yamaguchi esterification, see
-
For Yamaguchi esterification, see: Yamaguchi, M.; Innaga, J.; Hirata, K.; Saeki, H.; Katsuki, T. Bull. Chem. Soc. Jpn. 1979, 52, 1989-1993.
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(1979)
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Yamaguchi, M.1
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Hirata, K.3
Saeki, H.4
Katsuki, T.5
-
55
-
-
72849109802
-
-
In other routes involving similar coupling, the C-8 OH was all masked as either a TBS ether or an acetate (ref 2a,g,f).
-
In other routes involving similar coupling, the C-8 OH was all masked as either a TBS ether or an acetate (ref 2a,g,f).
-
-
-
-
56
-
-
0000865359
-
-
Lal, B.; Pramanik, E. N.; Manhas, M. S.; Bose, A. K. Tetrahedron Lett. 1977, 1977-1980.
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Lal, B.1
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-
58
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72849134281
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-
3
-
3!
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