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1242296319
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3
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23844506416
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Total synthesis, see: a, 11254 and references cited therein. Formal total synthesis, see
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Total synthesis, see: (a) Jiang, X.; Garcia-Fortanet, J.; De Brabander, J. K. J. Am. Chem. Soc. 2005, 127, 11254 and references cited therein. Formal total synthesis, see:
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Jiang, X.1
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33947578914
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1093. Fragment syntheses, see
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(b) Ning, S.; Kiren, S.; Williams, L. J. Org. Lett. 2007, 9, 1093. Fragment syntheses, see:
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Ning, S.1
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22244436600
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2905. Analogue synthesis, see
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0033575406
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6 was prepared from commercially available 2,4,6-trimethoxytoluene in two steps in 46% yield according to literature procedure. Solladie, G.: Gehrold, N.; Maignan, J. Tetrahedron: Asymmetry 1999, 10, 2739.
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6 was prepared from commercially available 2,4,6-trimethoxytoluene in two steps in 46% yield according to literature procedure. Solladie, G.: Gehrold, N.; Maignan, J. Tetrahedron: Asymmetry 1999, 10, 2739.
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12
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0001015876
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Parmee, E. R.; Tempkin, O.; Masamune, S. J. Am. Chem. Soc. 1991, 113, 9365.
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0034602349
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14
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34547182301
-
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Although we did not proceed with compound 3 for the total synthesis, it was prepared efficiently from 14 in 7 steps (Scheme 4) and served as a vehicle to determine the correct sterochemistry at C5 by spectrum comparison with the psymberin side chain.2d,e
-
2d,e
-
-
-
-
15
-
-
34547195715
-
-
All compounds containing this side chain were a 1:1 mixture of two isomers (R, S) at C: except when otherwise indicated.
-
All compounds containing this side chain were a 1:1 mixture of two isomers (R, S) at C: except when otherwise indicated.
-
-
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16
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28244443391
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Maffioli, S. I.; Marzorati, E.; Marazzi, A. Org. Lett. 2005, 7, 5237.
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0035823879
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and references cited therein
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Evans, D. A.; Allison, B. D.; Yang, M. O.; Masse, C. E. J. Am. Chem. Soc. 2001, 123, 10840 and references cited therein.
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Masse, C.E.4
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19
-
-
34547178752
-
-
15 acetonide from the corresponding hydroxy derivatives of 18.
-
15 acetonide from the corresponding hydroxy derivatives of 18.
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20
-
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33845373603
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Takai, K.; Nitta, K.; Utimoto, K. J. Am. Chem. Soc. 1986, 108, 7408.
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21
-
-
34547189098
-
-
It is not necessary to separate the E and Z isomers since they work equally well in the oxidative cyclization reaction. See ref 3
-
It is not necessary to separate the E and Z isomers since they work equally well in the oxidative cyclization reaction. See ref 3.
-
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22
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0142106421
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23
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-
34547177710
-
-
The R,R stereochemistry at Cx, CY was assigned by using COSY, NOESY, HSQC, and HMBC experiments with the final product epi-1, see the Supporting Information.
-
The R,R stereochemistry at Cx, CY was assigned by using COSY, NOESY, HSQC, and HMBC experiments with the final product epi-1, see the Supporting Information.
-
-
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24
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0001007594
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