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a) For a particularly instructive case see: K. Biswas, H. Lin, J. T. Njardarson, M. D. Chappell, T.-C. Chou, Y. Guan, W. P. Tong, L. He, S. B. Horwitz, S. J. Danishefsky, J. Am. Chem. Soc. 2002, 124, 9825-9832;
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33748519855
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note
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Small amounts (10-15%) of the regioisomeric alkenylstannane could be separated by flash chromatography. The corresponding pinacolborane was also prepared but failed to undergo productive cross-coupling with iodide 30.
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33748573963
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This route to 27 was chosen for two reasons: first, problems with partial racemization were encountered when the aldehyde derived from 23 was treated with Wittig reagents in an attempt to form 28 directly; secondly, it is known that iejimalide B bearing a methyl group at C2 is more active than iejimalide A which features a proton at this position, see Ref. [2]; the chosen route via triflate 27 allows for systematic variations at this position.
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Worried that reversible double-bond isomerizations at the aldehyde stage or an equilibrium between 30 and 31 would racemize the chiral center at C4, the ee value of compound 30 was carefully checked and found to be ≥ 90%.
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33748525507
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note
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Uncontrolled isomerizations were observed even at 35°C.
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71
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Significant amounts of the symmetrical anhydride derived from acid 33 could even be isolated from the mixture; for precedents and a mechanistic discussion see: I. Dhimitruka, J. SantaLucia, Jr., Org. Lett. 2006, 8, 47-50.
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