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1
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0343811402
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This project was completed in August 1993 and was presented at seminars by REI at Harvard (October, 1993) and by LL at Columbia (October, 1994)
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(a) This project was completed in August 1993 and was presented at seminars by REI at Harvard (October, 1993) and by LL at Columbia (October, 1994).
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2
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0342940479
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Taken in part from the PhD Thesis of TDR, University of Virginia, 1991
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(b) Taken in part from the PhD Thesis of TDR, University of Virginia, 1991.
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3
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0023245677
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(a) Kino, T.; Hatanaka, H.; Hashimoto, M.; Nishiyama, M.; Goto, T.; Okuhara, M.; Kohsaka, M.; Aoki, H.; Imanaka, H. J. Antibiotics 1987, 40, 1249.
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Okuhara, M.6
Kohsaka, M.7
Aoki, H.8
Imanaka, H.9
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4
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0023261356
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(b) Kino, T.; Hatanaka, H.; Miyata, S.; Inamura, N.; Nishiyama, M.; Toshimi, Y.; Goto, T.; Okuhara, M.; Kohsaka, M.; Aoki, H.; Ochia, T. J. Antibiotics 1987, 40, 1256.
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Kino, T.1
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Toshimi, Y.6
Goto, T.7
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Kohsaka, M.9
Aoki, H.10
Ochia, T.11
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5
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0001870609
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See, for example: Belshaw, P. J.; Meyer, S. D.; Johnson, D. D.; Romo, D.; Ikeda, Y.; Andrus, M.; Alberg, D. G.; Schulz, L. W.; Clardy, J.; Schreiber, S. L. Synlett 1994, 381.
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Synlett
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Andrus, M.6
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Schreiber, S.L.10
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6
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0343811391
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(b) ref. 4(a)
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14
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85064631783
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and references cited therein
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(a) For a compilation of the eariler synthetic studies, see: White, J. D.; Toske, S. G.; Yakura, T. Synlett 1994, 591 and references cited therein.
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Synlett
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White, J.D.1
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17
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(c) Nakatsuka, M.; Ragan, J. A.; Sammakia, T.; Smith, D. B.; Uehling, D. E.; Schreiber, S. L. J. Am. Chem. Soc. 1990,112, 5583.
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It should be pointed out that Stork's ancillary stereocontrol strategy should be applicable in terms of correcting the C24 stereochemistry via, for example, structure i: Stork, G.; Paterson, I.; Lee, F. K. C. J. Am. Chem. Soc. 1982, 104, 4686. (formula presented)
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0342940453
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note
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3·ether, 50 °C, 78%).
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47
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0013286080
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2 was employed to open the epoxide of methyl 2,3-anhydro-5-deoxy-α-L-lyxofuranoside: Fleet, G. W. J.; Shing, T. K. M. Tetrahedron Lett. 1983, 24, 3657.
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0342506157
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Lindberg, T. Ed.; Academic: New York, Chapter 11
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, pp. 650
-
-
Ireland, R.E.1
Wipf, P.2
Armstrong J.D. III3
-
85
-
-
0000833130
-
-
Bertz, S. H.; Gibson, C. P.; Dabbagh, G. Tetrahedron Lett. 1987, 28, 4251.
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(1987)
Tetrahedron Lett.
, vol.28
, pp. 4251
-
-
Bertz, S.H.1
Gibson, C.P.2
Dabbagh, G.3
-
86
-
-
84989456730
-
-
For a recent review, see, Einhorn, K.; Einhorn, J.; Luche, J. Synthesis 1989, 787.
-
(1989)
Synthesis
, pp. 787
-
-
Einhorn, K.1
Einhorn, J.2
Luche, J.3
-
87
-
-
0343375772
-
-
Ref. 45
-
(a) Ref. 45.
-
-
-
-
88
-
-
0024464991
-
-
(b) Ragan, J. A.; Nakatsuka, M.; Smith, D. B.; Uehling, D. E.; Schreiber, S. L. J. Org. Chem. 1989, 54, 4267.
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(1989)
J. Org. Chem.
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-
Ragan, J.A.1
Nakatsuka, M.2
Smith, D.B.3
Uehling, D.E.4
Schreiber, S.L.5
-
89
-
-
0342940417
-
-
note
-
1H NMR spectra of each sample with those of 38 (cf. Scheme 8) indicates that the sample derived from the major isomer possesses the desired α-OH at C26.
-
-
-
-
90
-
-
0343811342
-
-
3, MeOH, -78 °C
-
3, MeOH, -78 °C.
-
-
-
-
91
-
-
0343811341
-
-
3, MeOH-ether, -70 °C; cf. Kishi and coworkers, J. Am. Chem. Soc. 1989, 111, 7525.
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(1989)
J. Am. Chem. Soc.
, vol.111
, pp. 7525
-
-
Kishi1
-
92
-
-
0342506118
-
-
4, THF, -78-0 °C
-
4, THF, -78-0 °C.
-
-
-
-
93
-
-
0342940415
-
-
DIBALH, PhMe, -78 °0C
-
(d) DIBALH, PhMe, -78 °0C.
-
-
-
-
94
-
-
0343375767
-
-
RedAl, THF or PhMe, rt
-
(e) RedAl, THF or PhMe, rt.
-
-
-
-
95
-
-
0009639022
-
-
2, ether, -78 °C; cf. Tamura, Y.; Annoura, H.; Fujioka, H. Tetrahedron Lett. 1987, 28, 5681.
-
(1987)
Tetrahedron Lett.
, vol.28
, pp. 5681
-
-
Tamura, Y.1
Annoura, H.2
Fujioka, H.3
-
96
-
-
84990541303
-
-
2, ether, rt; cf. Kamitori, K.; Hojo, M.; Masuda, R.; Izumi, T.; Inoue, T. Synthesis 1983, 387.
-
(1983)
Synthesis
, pp. 387
-
-
Kamitori, K.1
Hojo, M.2
Masuda, R.3
Izumi, T.4
Inoue, T.5
-
97
-
-
85011198481
-
-
4, ether, 0 °C; cf. Nakata, T.; Tani, Y.; Hatozaki, M.; Oishi, T. Chem. Pharm. Bull. 1984, 32, 1411. Also ref. 9(b)).
-
(1984)
Chem. Pharm. Bull.
, vol.32
, pp. 1411
-
-
Nakata, T.1
Tani, Y.2
Hatozaki, M.3
Oishi, T.4
-
98
-
-
0343811336
-
-
LAH, ether, -78 or -100 °C (2:1)
-
Conditions that led to the formation of ≤2:1 β, α-isomer: (i) LAH, ether, -78 or -100 °C (2:1)
-
-
-
-
99
-
-
0342349528
-
-
3, THF, -78 °C (2:1); cf. Fukuzawa, S.-i.; Fujinami, T.; Yamauchi, S.; Sakai, S. J. Chem. Soc. Perkin Trans. I 1986, 1929.
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(1986)
J. Chem. Soc. Perkin Trans. I
, pp. 1929
-
-
Fukuzawa, S.-I.1
Fujinami, T.2
Yamauchi, S.3
Sakai, S.4
-
100
-
-
0342940413
-
-
LAH, LiBr, ether, -78 °C (2:1 plus what seemed to be a 1,3-allylic rearranged product)
-
(k) LAH, LiBr, ether, -78 °C (2:1 plus what seemed to be a 1,3-allylic rearranged product).
-
-
-
-
101
-
-
0001164834
-
-
(l) LAH, LiI, ether, -78 °C (2:1), -100 °C (1:1); cf. Mori, Y.; Kuhara, M.; Takeuchi, A.; Suzuki, M.Tetrahedron Lett. 1988, 29, 5419.
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(1988)
Tetrahedron Lett.
, vol.29
, pp. 5419
-
-
Mori, Y.1
Kuhara, M.2
Takeuchi, A.3
Suzuki, M.4
-
102
-
-
0025068753
-
-
The asymmetric catalyst system (S)-α,α-diphenyl-B-butyloxazoborolidine-catecholborane-PhMe did not react with enone 45 (-78 °C to rt), see: (m) Corey, E. J.; Bakshi, R. K. Tetrahedron Lett. 1990, 31, 611.
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(1990)
Tetrahedron Lett.
, vol.31
, pp. 611
-
-
Corey, E.J.1
Bakshi, R.K.2
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103
-
-
0343811335
-
-
Wiley: New York, Chapter 2
-
Hughes, D. L. in Org. Reactions; Wiley: New York, 1992; Vol. 42, Chapter 2.
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(1992)
Org. Reactions
, vol.42
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Hughes, D.L.1
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104
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0002714675
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(a) Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923.
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J. Org. Chem.
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, pp. 2923
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Still, W.C.1
Kahn, M.2
Mitra, A.3
-
106
-
-
0344743411
-
-
Watson, S. C.; Eastham, J. F. J. Organomet. Chem. 1967, 9, 165. For a newer method, see, Winkle, M. R.; Lansinger, J. M.; Ronald, R. C. J. Chem. Soc., Chem. Commun. 1980, 87.
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J. Organomet. Chem.
, vol.9
, pp. 165
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Watson, S.C.1
Eastham, J.F.2
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107
-
-
0003036944
-
-
Watson, S. C.; Eastham, J. F. J. Organomet. Chem. 1967, 9, 165. For a newer method, see, Winkle, M. R.; Lansinger, J. M.; Ronald, R. C. J. Chem. Soc., Chem. Commun. 1980, 87.
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(1980)
J. Chem. Soc., Chem. Commun.
, pp. 87
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Winkle, M.R.1
Lansinger, J.M.2
Ronald, R.C.3
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109
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33744586503
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Miyashita, N.; Yoshikoshi, A.; Grieco, P. A. J. Org. Chem. 1977, 42, 3772.
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Miyashita, N.1
Yoshikoshi, A.2
Grieco, P.A.3
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110
-
-
0000776391
-
-
Corey, E. J.; Cho, H.; Rücker, C.; Hua, D. Tetrahedron Lett. 1981, 22, 3455.
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(1981)
Tetrahedron Lett.
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Corey, E.J.1
Cho, H.2
Rücker, C.3
Hua, D.4
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