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11
-
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0342733238
-
-
note
-
Thyrsiferol (1b), 15(28)-anhydrothyrsiferyl-23-acetate (2a), thyrsiferyl 18-acetate (1c), and thyrsiferyl 15, 18, 23-triacetate.
-
-
-
-
12
-
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0033018282
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(a) Matsuzawa, S.-I.; Kawamura, T.; Mitsuhashi, S.; Suzuki, T.; Matsuo, Y.; Suzuki, M.; Mizuno, Y.; Kikuchi, K. Bioorg. Med. Chem. 1999, 7, 381-387.
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Kikuchi, K.1
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15
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0028985934
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(a) Uckun, F. M.; Evans, W. E.; Forsyth, C. J.; Waddick, K. G.; Ahlgren, L. T.; Chelstrom, L. M.; Burkhardt, A.; Bolen, J.; Myers, D. E. Science 1995, 267, 886-891.
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16
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0028846718
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(b) Myers, D. E.; Jun, X.; Waddick, K. G.; Chelstrom, L. M.; Forsyth, C. J.; Gunther, R.; Turner, N.; Bolen, J.; Uckun, F. M. Proc. Natl. Acad. Sci. USA 1995, 9575-9579.
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Uckun, F.M.9
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17
-
-
0028950664
-
-
50 PP2A = 3.2-40 nM (Roberge, M.; Tudan, C.; Hung, S. M. F.; Harder, K. W.; Jirik, F. R.; Anderson, H. Cancer Res. 1994, 54, 6115-6121; Walsh, A. H.; Cheng, A.; Honkanen, R. E. FEBS Lett. 1997, 416, 230-234).
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18
-
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0023691731
-
-
50 PP2A = 3.2-40 nM (Roberge, M.; Tudan, C.; Hung, S. M. F.; Harder, K. W.; Jirik, F. R.; Anderson, H. Cancer Res. 1994, 54, 6115-6121; Walsh, A. H.; Cheng, A.; Honkanen, R. E. FEBS Lett. 1997, 416, 230-234).
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Bialojan, C.1
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19
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0028063201
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50 PP2A = 3.2-40 nM (Roberge, M.; Tudan, C.; Hung, S. M. F.; Harder, K. W.; Jirik, F. R.; Anderson, H. Cancer Res. 1994, 54, 6115-6121; Walsh, A. H.; Cheng, A.; Honkanen, R. E. FEBS Lett. 1997, 416, 230-234).
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Roberge, M.1
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Anderson, H.6
-
20
-
-
0030720062
-
-
50 PP2A = 3.2-40 nM (Roberge, M.; Tudan, C.; Hung, S. M. F.; Harder, K. W.; Jirik, F. R.; Anderson, H. Cancer Res. 1994, 54, 6115-6121; Walsh, A. H.; Cheng, A.; Honkanen, R. E. FEBS Lett. 1997, 416, 230-234).
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23
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0031814730
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25
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0343167748
-
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note
-
50 1c = 464 nM. 2
-
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26
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0023636077
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0023633185
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0023930482
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0001160421
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0000786794
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33845375686
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0000959935
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0013056648
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0001211286
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47
-
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0343603167
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-
note
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This approximate yield was obtained after purification of the crude mixture through a short silica gel column; further purification using MPLC caused loss of material.
-
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-
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48
-
-
0343167746
-
-
note
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The ratio was determined by GC using a DBS column (10m × 0.1 mm × 0.1 μm film thickness).
-
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50
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0027502970
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0000346999
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18844410382
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33748630895
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63
-
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0342733230
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note
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The corresponding cis epoxides have been shown to disfavor the 6-endo mode of ring closure.
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64
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0025289014
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0028354092
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0001339910
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A diastereomer of the aldehyde 28 was prepared previously from L-glutamic acid: Nicolaou, K. C.; Reddy, K. J.; Skokotas, G.; Sato, F.; Xiao, X.-Y.; Hwang, C.-K. J. Am. Chem. Soc. 1993, 115, 3558-3575.
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0342733226
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note
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For a precedent of this reaction in a cis dibromoalkenyl epoxide, see ref 35.
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Sharpless, K. B.; Amberg, W.; Bennani, Y. L.; Crispino, G. A.; Hartung, J.; Jeong, K.-S.; Kwong, H.-L.; Morikawa, K.; Wang, Z.-M.; Xu, D.; Zhang, X.-L. J. Org. Chem. 1992, 57, 2768-2771.
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Sharpless, K.B.1
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Hartung, J.5
Jeong, K.-S.6
Kwong, H.-L.7
Morikawa, K.8
Wang, Z.-M.9
Xu, D.10
Zhang, X.-L.11
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82
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0342298251
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note
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The stereochemistry of tetrahydrofurans 40 was determined at the stage of the diacetate derivatives. The diacetate 46, derived from 40a, showed an NOE between protons al the C18 and C22 positions (Scheme 8).
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83
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0027371818
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Vidari, G.; Dapiaggi, A.; Zanoni, G.; Garlaschelli, L. Tetrahedron Lett. 1993, 34, 6485-6488.
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, pp. 6485-6488
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Vidari, G.1
Dapiaggi, A.2
Zanoni, G.3
Garlaschelli, L.4
-
84
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-
0343603157
-
-
note
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The stereochemistry of the trans-tetrahydrofuran 41a was determined after protecting the two free hydroxyls with MOM groups, by detection of an NOE between protons at the C18 and C22 positions.
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-
-
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85
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85011245852
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Ishihara, K.; Kubota, M.; Kurihara, H.; Yamamoto, H. J. Am. Chem. Soc. 1995, 117, 4413-4414.
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Ishihara, K.1
Kubota, M.2
Kurihara, H.3
Yamamoto, H.4
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86
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0032500348
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Sinha, S. C.; Keinan, E.; Sinha, S. C. J. Am. Chem. Soc. 1998, 120, 9076-9077.
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Sinha, S.C.1
Keinan, E.2
Sinha, S.C.3
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87
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0031437614
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Sinha, S. C.; Sinha, A.; Sinha, S. C.; Keinan, E. J. Am. Chem. Soc. 1997, 119, 12014-12015.
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Sinha, S.C.1
Sinha, A.2
Sinha, S.C.3
Keinan, E.4
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89
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0001333219
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(a) Herrmann, W. A.; Thiel, W. R.; Kühn, F. E.; Fischer, R. W.; Kleine, M.; Herdtweck, E.; Scherer, W. Inorg. Chem. 1993, 32, 5188-5194.
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Herrmann, W.A.1
Thiel, W.R.2
Kühn, F.E.3
Fischer, R.W.4
Kleine, M.5
Herdtweck, E.6
Scherer, W.7
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91
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33845373603
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Takai, K.; Nitta, K.; Utimoto, K. J. Am. Chem. Soc. 1986, 108, 7408-7410.
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Takai, K.1
Nitta, K.2
Utimoto, K.3
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92
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0342733225
-
-
note
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1H NMR determination of the crude mixture it was possible to distinguish the two possible isomers in the ratio 3:1; however, the stereochemistry at the C15 was not assigned.
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-
-
-
95
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84989092672
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-
and ref 14d
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1H NMR and HRMS data of 1b and 1a matched those previously reported: Blunt, J. W.; McCombs, J. D.; Munro, M. H. G.; Thomas, F. N. Magn. Reson. Chem. 1989, 27, 792-795 and ref 14d.
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-
Blunt, J.W.1
McCombs, J.D.2
Munro, M.H.G.3
Thomas, F.N.4
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96
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0342298250
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note
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1H NMR spectrum of semisynthetic 1c obtained from a natural sample of 1b, which was kindly provided by Prof. J. W. Blunt.
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