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33751500471
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85034118836
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note
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13C NMR spectra, as well as appropriate ion identification by high-resolution mass spectrometry.
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21
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0013621385
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23
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85034125461
-
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note
-
A nuclear Overhauer enhancement was observed between H(5) and H(7); irradiation of H(5) did not enhance the H(9) resonance.
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25
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0000376088
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(a) Carreira, E. M.; Singer, R. A.; Lee, W. J. Am. Chem. Soc. 1994, 116, 8837.
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33751391553
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(b) Smrcina, M.; Lorenc, M.; Hanus, V.; Sedmera, P.; Kocovsky, P. J. Org. Chem. 1992, 57, 1917.
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Smrcina, M.1
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33947086629
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4243825385
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84987472577
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33
-
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85034145545
-
-
note
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2.
-
-
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-
34
-
-
85034138210
-
-
note
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See Supporting Information.
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-
-
-
35
-
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85034153415
-
-
note
-
2AlCl was effective.
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-
-
-
36
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0033546101
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2AlCl, see: Evans, D. A.; Allison, B. D.; Yang, M. G. Tetrahedron Lett. 1999, 40, 4457.
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Evans, D.A.1
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38
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0028886765
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39
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0023639370
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Boeckman, R. K., Jr.; Charette, A. B.; Asberom, T.; Johnston, B. H. J. Am. Chem. Soc. 1987, 109, 7553.
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Boeckman R.K., Jr.1
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0000016331
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Danishefsky, S.1
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42
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85034125724
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note
-
Enantiomeric excess was determined at the level of (-)-24 by 500 MHz NMR analysis of the diastereomeric ratio.
-
-
-
-
43
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0000526264
-
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Interestingly, when the reaction was performed at 0°C, ketone reduction was competitive with hydroboration
-
Evans, D. A.; Fu, G. C.; Hoveyda, A. H. J. Am. Chem. Soc. 1992, 114, 6671. Interestingly, when the reaction was performed at 0°C, ketone reduction was competitive with hydroboration.
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Evans, D.A.1
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Hoveyda, A.H.3
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44
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37049091522
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Nagao, Y.; Yamada, S.; Kumagai, T.; Ochiai, M.; Fujita, E. J. Chem. Soc. Chem. Commun. 1985, 20, 1418.
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Nagao, Y.1
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Kumagai, T.3
Ochiai, M.4
Fujita, E.5
-
45
-
-
85034124346
-
-
note
-
The absolute configuration at C(11) was secured by Mosher ester analysis; see ref 13.
-
-
-
-
46
-
-
85034142548
-
-
note
-
Mutual nuclear Overhauer enhancements of the H(11) and H(15) resonances indicated the cis relationship in tetrahydropyran (-)-27.
-
-
-
-
47
-
-
85034130984
-
-
note
-
4) would provide access to phorboxazole B.
-
-
-
-
48
-
-
85034124219
-
-
note
-
The iodide was moderately unstable and thus used immediately.
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