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3
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70350612065
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Leading references for the total synthesis of amphidinolides: Amphidinolide A
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Leading references for the total synthesis of amphidinolides: Amphidinolide A:
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9
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Amphidinolide H-G: e) A. Fürstner, L. C. Bouchez, J.-A. Funěl, V. Liepins, F-H. Porée, R. Gilmour, F. Beaufils, D. Laurich, M. Tamiya, Angew. Chem. 2007, 119, 9425-9430;
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70350601582
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Alternative synthesis of compound 9 starting with a TBSprotected alkyl iodide (8') gave lower yields and poor diastereomeric ratios. The TBDPS to TBS swap was necessary to allow further functional group manipulations at a later stage of the synthesis
-
Alternative synthesis of compound 9 starting with a TBSprotected alkyl iodide (8') gave lower yields and poor diastereomeric ratios. The TBDPS to TBS swap was necessary to allow further functional group manipulations at a later stage of the synthesis.
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32
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70350598684
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Benzyl ether removal in presence of the free acid, even under neutral conditions, led to partial lactonization of the resulting alcohol
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Benzyl ether removal in presence of the free acid, even under neutral conditions, led to partial lactonization of the resulting alcohol.
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34
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35
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85027732552
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For the formation of the diol 5a, see a
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For the formation of the diol 5a, see a) M. A. Robbins, P. N. Devine, T. Oh, Org. Synth. 1999, 76, 101-109;
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b) C. C. Marvin, A. J. L. Clemens, S. D. Burke, Org. Lett. 2007, 9, 5353-5356;
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Marvin, C.C.1
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37
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17444416491
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for the preparation of 5b and 5c, see: c) K. J. Quinn, A. K. Isaacs, B. A. DeChristopher, S. C. Szklarz, R. A. Arvary, Org. Lett. 2005, 7, 1243-1245.
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70350577877
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For further details, see the Supporting Information
-
For further details, see the Supporting Information.
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40
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28844501313
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and references therein
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See reference [16c] and also: S. Michaelis, M. Blechert, Org. Lett. 2005, 7, 5513-5516, and references therein.
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Michaelis, S.1
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41
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70350611908
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Compounds 22a and 22b could be separated at this stage to give a 2:1 ratio, confirming the E configuration of the olefin produced in the CM event
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Compounds 22a and 22b could be separated at this stage to give a 2:1 ratio, confirming the E configuration of the olefin produced in the CM event.
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42
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33847081223
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A single successful precedent for such transformation is reported using TASF: R. Lira, W. R. Roush, Org. Lett. 2007, 9, 533-536.
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