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3
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0001048203
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See the following for leading references on studies towards related farnesyl phenol natural products; some of them further illustrate the difficulties arising in the final deprotection steps of the aryl ether groups: (a) Chen, K.-M.; Semple, J. E.; Joullié, M. M. J. Org. Chem. 1985, 50, 3997.
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Joullié, M.M.3
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0022491999
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(b) Safaryn, J. E.; Chiarello, J.; Chen, K.-M.; Joullié, M. M. Tetrahedron 1986, 42, 2635.
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Safaryn, J.E.1
Chiarello, J.2
Chen, K.-M.3
Joullié, M.M.4
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5
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Guthrie, A. E.; Semple, J. E.; Joullié, M. M. J. Org. Chem. 1982, 47, 2369.
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Semple, J.E.2
Joullié, M.M.3
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10
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0032485365
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Only a few general methods for the preparation of 2,4-disubstituted furans are known; for a review see: Hou, X. L.; Cheung, H. Y.; Hon, T. Y.; Kwan, P. L.; Lo, T. H.; Tong, S. Y.; Wong, H. N. C. Tetrahedron 1998, 54, 1955.
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Hou, X.L.1
Cheung, H.Y.2
Hon, T.Y.3
Kwan, P.L.4
Lo, T.H.5
Tong, S.Y.6
Wong, H.N.C.7
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11
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0041132062
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See also the Supporting Information for a multigram synthesis of this compound
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Barrett, A. G. M.; Morris, T. M.; Barton, D. H. R. J. Chem. Soc., Perkin Trans. 1 1980, 2272. See also the Supporting Information for a multigram synthesis of this compound.
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J. Chem. Soc., Perkin Trans. 1
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Barrett, A.G.M.1
Morris, T.M.2
Barton, D.H.R.3
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85008739003
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Ishii, N.; Takahashi, A.; Kusano, G.; Nozoe, S. Chem. Pharm. Bull. 1988, 36, 2918.
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Ishii, N.1
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Nozoe, S.4
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16
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85037504234
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note
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Silyl ethers instead of SEM groups were ruled out for the reason given in ref 19.
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17
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0001215084
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Saimoto, H.; Kusano, Y.; Hiyama, T. Tetrahedron Lett. 1986, 27, 1607.
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Saimoto, H.1
Kusano, Y.2
Hiyama, T.3
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18
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85037515475
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note
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For details see the Supporting Information.
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20
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0033537059
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(b) Fürstner, A.; Guth, O.; Rumbo, A.; Seidel, G. J. Am. Chem. Soc. 1999, 121, 11108.
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Fürstner, A.1
Guth, O.2
Rumbo, A.S.G.3
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24
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0033515494
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Fürstner, A.; Gastner, T.; Weintritt, H. J. Org. Chem. 1999, 64, 2361.
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Fürstner, A.1
Gastner, T.2
Weintritt, H.3
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26
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0039697372
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2O, rt, 77%) in analogy to a procedure described in: Garner, P.; Park, J. M. Synth. Commun. 1987, 17, 189.
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Garner, P.1
Park, J.M.2
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27
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0000422811
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For leading references on Pd(0)-catalyzed reactions of vinyloxiranes, see: (a) Tsuji, J.; Kataoka, H.; Kobayashi, Y. Tetrahedron Lett. 1981, 22, 2575.
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Tetrahedron Lett.
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Tsuji, J.1
Kataoka, H.2
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31
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85037516397
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note
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Compounds 10-12 are obtained as mixtures of stereoisomers. Since all of them converge into product 13, the synthesis depicted in Scheme 2 was carried out with these mixtures and no attempts were made to isolate the individual isomers.
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32
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0000192963
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(a) Oikawa, Y.; Yoshioka, T.; Yonemitsu, O. Tetrahedron Lett. 1982, 23, 885.
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Oikawa, Y.1
Yoshioka, T.2
Yonemitsu, O.3
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33
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85037518330
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note
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(b) At this point it is essential to have chosen a PMB group rather than a simple Bn ether as the protecting group for the benzylic alcohol. All attempts to cleave the corresponding benzyl ether failed to afford the desired product 14. For example, attempted hydrogenation over Pd/C reduces the furan ring without cleaving the benzyl ether.
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34
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0028064765
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Yu, J.; Cho, H.-S.; Chandrasekhar, S.; Falck, J. R.; Mioskowski, C. Tetrahedron Lett. 1994, 35, 5437.
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Yu, J.1
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Falck, J.R.4
Mioskowski, C.5
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35
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85037521481
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note
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Note that attempted alkylations of the metalated sulfone with an allyl bromide analogous to 7 carrying -OTBDMS instead of -OSEM groups gave the desired compound in less than 5% yield.
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36
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49549126692
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Trost, B. M.; Arndt, H. C.; Strege, P. E.; Verhoeven, T. R. Tetrahedron Lett. 1976, 3477.
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Kan, T.; Hashimoto, M.; Yanagiya, M.; Shirahama, H. Tetrahedron Lett. 1988, 29, 5417.
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0032569211
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For previous studies on bioactive heterocycles from our laboratory, see: (a) Fürstner, A.; Szillat, H.; Gabor, B.; Mynott, R. J. Am. Chem. Soc. 1998, 120, 8305.
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(e) Fürstner, A.; Weintritt, H.; Hupperts, A. J. Org. Chem. 1995, 60, 6637.
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(g) Fürstner, A.; Grabowski, J.; Lehmann, C. W. J. Org. Chem. 1999, 64, 8275.
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