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note
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The reaction utilizing Boc-amino acids provided reaction mixtures with fewer side products.
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45
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33544469851
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note
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In all cases where we have used conventional heating to generate intermediates corresponding to 19, microwave heating could generate the same products, albeit in lower yields.
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46
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33544456990
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note
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As a comparison, a control reaction was carried out in a sealed tube under conventional heating in an oil bath at 210 °C (the minimal temperature required for the reaction to proceed) for 15 min. The product 2 was formed, but the crude reaction mixture was more complex with multiple side products and fully racemized products (LC/MS, ELSD = 60%, ee = 0%) as compared with the microwave conditions which provided the product in higher yield with minimal side reactions and with much less enantiomeric erosion (LC/MS, ELSD = 75%, ee = 70%). Additionally, the conventional heating conditions (sealed tube) are not practical for parallel synthesis of analogue libraries of the natural products, which is an effort that we are pursuing.
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47
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note
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The synthesis of 3 was also achieved with the use of D-tryptophan methylester, resulting in an identical yield and optical purity under the same microwave conditions as those used for D-tryptophan methylester hydrochloride (10d).
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48
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33544457738
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note
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13C NMR relative to enantiomerically pure 3.
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49
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33544463421
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note
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1H NMR is identical with fumiquinazoline G in ref 9b. The chiral SFC/MS analysis confirmed that it is a racemate of 4.
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50
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33544456687
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note
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3)}. See the Experimental Section for details.
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51
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0035956415
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See ref 10b
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Steric hindrance is an important factor in unsuccessful quinazolinone ring formation in Fiscalin B total synthesis. See the discussion in: Buenadicha, F. L.; Avendaño, C.; Söllhuber, M. Tetrahedron: Asymmetry 2001, 12, 3019. See ref 10b.
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Tetrahedron: Asymmetry
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Buenadicha, F.L.1
Avendaño, C.2
Söllhuber, M.3
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Goetzinger, W.; Zhang, X.; Bi, G.; Towle, M.; Cherrak, D.; Kyranos, J. N. Int. J. Mass. Spectrom. 2004, 238, 153.
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Goetzinger, W.1
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Bi, G.3
Towle, M.4
Cherrak, D.5
Kyranos, J.N.6
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