-
1
-
-
0032582026
-
-
Satake, M.; Ofuji, K.; Naoki, H.; James, K. J.; Furey, A.; McMahon, T.; Silke, J.; Yasumoto, T. J. Am. Chem. Soc. 1998, 120, 9967.
-
(1998)
J. Am. Chem. Soc.
, vol.120
, pp. 9967
-
-
Satake, M.1
Ofuji, K.2
Naoki, H.3
James, K.J.4
Furey, A.5
McMahon, T.6
Silke, J.7
Yasumoto, T.8
-
2
-
-
0033390733
-
-
Ofuji, K.; Satake, M.; McMahon, T.; Silke, J.; James, K. J.; Naoki, H.; Oshima, Y.; Yasumoto, T. Nat. Toxins 1999, 7, 99.
-
(1999)
Nat. Toxins
, vol.7
, pp. 99
-
-
Ofuji, K.1
Satake, M.2
McMahon, T.3
Silke, J.4
James, K.J.5
Naoki, H.6
Oshima, Y.7
Yasumoto, T.8
-
3
-
-
0033580904
-
-
For a review of bis-spiroketal natural products and their syntheses see: (a) Brimble, M. A.; Farès, F. A. Tetrahedron 1999, 55, 7661.
-
(1999)
Tetrahedron
, vol.55
, pp. 7661
-
-
Brimble, M.A.1
Farès, F.A.2
-
4
-
-
0032486789
-
-
(b) McCauley, J. A.; Nagasawa, K.; Lander, P. A.; Mischke, S. G.; Semones, M. A.; Kishi, Y. J. Am. Chem. Soc. 1998, 120, 7647.
-
(1998)
J. Am. Chem. Soc.
, vol.120
, pp. 7647
-
-
McCauley, J.A.1
Nagasawa, K.2
Lander, P.A.3
Mischke, S.G.4
Semones, M.A.5
Kishi, Y.6
-
6
-
-
0035966587
-
-
(b) Aiguade, J.; Hao, J.; Forsyth, C. J. Tetrahedron Lett. 2001, 42, 817.
-
(2001)
Tetrahedron Lett.
, vol.42
, pp. 817
-
-
Aiguade, J.1
Hao, J.2
Forsyth, C.J.3
-
7
-
-
0035966571
-
-
(c) Hao, J.; Aiguade, J.; Forsyth, C. J. Tetrahedron Lett. 2001, 42, 821.
-
(2001)
Tetrahedron Lett.
, vol.42
, pp. 821
-
-
Hao, J.1
Aiguade, J.2
Forsyth, C.J.3
-
8
-
-
0035810370
-
-
(d) Aiguade, J.; Hao, J.; Forsyth, C. J. Org. Lett. 2001, 3, 979.
-
(2001)
Org. Lett.
, vol.3
, pp. 979
-
-
Aiguade, J.1
Hao, J.2
Forsyth, C.J.3
-
9
-
-
0030865642
-
-
A similar acid-triggered speroketalization was employed to install the dioxaspiro[4.5]nonane system of okadaic acid: Forsyth, C. J.; Sabes, S. F.; Urbanek, R. A. J. Am. Chem. Soc. 1997, 119, 8381.
-
(1997)
J. Am. Chem. Soc.
, vol.119
, pp. 8381
-
-
Forsyth, C.J.1
Sabes, S.F.2
Urbanek, R.A.3
-
10
-
-
0041789564
-
-
note
-
Numbering corresponds to that of 1-3.
-
-
-
-
12
-
-
0041289021
-
-
note
-
Compound 9 is commercially available from Aldrich Chemical Co., or it can be synthesized via addition of allylmagnesium bromide to acrolein.
-
-
-
-
13
-
-
33751499786
-
-
(a) Ireland, R. E.; Wipf, P.; Armstrong, J. D., III. J. Org. Chem. 1991, 56, 650.
-
(1991)
J. Org. Chem.
, vol.56
, pp. 650
-
-
Ireland, R.E.1
Wipf, P.2
Armstrong J.D. III3
-
15
-
-
33847799798
-
-
(c) Ireland, R. E.; Mueller, R. H.; Willard, A. K. J. Am. Chem. Soc. 1976, 98, 2868.
-
(1976)
J. Am. Chem. Soc.
, vol.98
, pp. 2868
-
-
Ireland, R.E.1
Mueller, R.H.2
Willard, A.K.3
-
16
-
-
0001646391
-
-
Either enantiomer of 9 is available in high % ee from the enantioselective allylation of acrolein with the appropriate B-allyldiisopinocampheylborane; see: Racherla, U. S.; Brown, H. C. J. Org. Chem. 1991, 56, 401.
-
(1991)
J. Org. Chem.
, vol.56
, pp. 401
-
-
Racherla, U.S.1
Brown, H.C.2
-
17
-
-
0141712450
-
-
(a) 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.
-
(1992)
J. Org. Chem.
, vol.57
, pp. 2768
-
-
Sharpless, K.B.1
Amberg, W.2
Bennani, Y.L.3
Crispino, G.A.4
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
-
18
-
-
4444276636
-
-
(b) For a review on Sharpless asymmetric dihydroxylation: Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483.
-
(1994)
Chem. Rev.
, vol.94
, pp. 2483
-
-
Kolb, H.C.1
VanNieuwenhze, M.S.2
Sharpless, K.B.3
-
19
-
-
0041289020
-
-
note
-
1H NMR spectroscopic analysis. This suggests that the poor diastereoselectivity does not simply result from intramolecular directing effects of the internal diol.
-
-
-
-
20
-
-
33751385752
-
-
Crispino, G. A.; Jeong, K.-S.; Kolb, H. C.; Wang, Z.-M.; Xu, D.; Sharpless, K. B. J. Org. Chem. 1993, 58, 3785.
-
(1993)
J. Org. Chem.
, vol.58
, pp. 3785
-
-
Crispino, G.A.1
Jeong, K.-S.2
Kolb, H.C.3
Wang, Z.-M.4
Xu, D.5
Sharpless, K.B.6
-
21
-
-
0033601363
-
-
(14)(a) Sasaki, M.; Inoue, M.; Takamatsu, K.; Tachibana, K. J. Org. Chem. 1999, 64, 9399.
-
(1999)
J. Org. Chem.
, vol.64
, pp. 9399
-
-
Sasaki, M.1
Inoue, M.2
Takamatsu, K.3
Tachibana, K.4
-
22
-
-
0030747943
-
-
(b) Matsukura, H.; Morimoto, M.; Koshino, H.; Nakata, T. Tetrahedron Lett. 1997, 38, 5545.
-
(1997)
Tetrahedron Lett.
, vol.38
, pp. 5545
-
-
Matsukura, H.1
Morimoto, M.2
Koshino, H.3
Nakata, T.4
-
24
-
-
0000215820
-
-
Corey, E. J.; Weisel, L. O.; Chamberlin, A. R.; Lipshutz, B. J. Am. Chem. Soc. 1980, 102, 1439. Hicks, D. R.; Fraser-Reid, B. Synthesis 1974, 203.
-
(1980)
J. Am. Chem. Soc.
, vol.102
, pp. 1439
-
-
Corey, E.J.1
Weisel, L.O.2
Chamberlin, A.R.3
Lipshutz, B.4
-
25
-
-
85065239587
-
-
Corey, E. J.; Weisel, L. O.; Chamberlin, A. R.; Lipshutz, B. J. Am. Chem. Soc. 1980, 102, 1439. Hicks, D. R.; Fraser-Reid, B. Synthesis 1974, 203.
-
(1974)
Synthesis
, pp. 203
-
-
Hicks, D.R.1
Fraser-Reid, B.2
-
26
-
-
0041288990
-
-
note
-
For convenience on a multigram scale, the mixture of 8 and 12 was typically used directly in the THF-rinng formation step, at which stage diol 7 was readily separated from its C19 epimer by column chromatography.
-
-
-
-
27
-
-
0041789538
-
-
note
-
2
-
-
-
-
28
-
-
0041288991
-
-
note
-
3CN, 24-48 h).
-
-
-
|